Skip to main content

Qiu Wang

Professor of Chemistry
Chemistry
Box 90346, 124 Science Drive, Durham, NC 27705
2102 French Science Center, Durham, NC 27705

Selected Publications


Celebrating the 130th anniversary of Wuhan University.

Journal Article Chemical science · February 2024 Lin Zhuang, Qiu Wang, Aiwen Lei and Qianghui Zhou introduce the Chemical Science and Green Chemistry joint themed collection celebrating the 130th Anniversary of Wuhan University. ... Full text Cite

Copper-Catalyzed Three-Component Aminofluorination of Alkenes and 1,3-Dienes: Direct Entry to Diverse β-Fluoroalkylamines.

Journal Article Journal of the American Chemical Society · November 2022 Rapid and efficient access to structurally diverse β-fluoroalkylamines is in high demand, with their wide presence and great importance in medicinal chemistry and drug development. Direct 1,2-aminofluorination of alkenes offers an ideal strategy for one-st ... Full text Cite

Design, synthesis and evaluation of 15N- and 13C-labeled molecular probes as hyperpolarized nitric oxide sensors.

Journal Article Bioorganic & medicinal chemistry · October 2022 Nitric oxide (NO) is an important signaling molecule involved in a wide range of biological processes. Development of non-invasive, real-time detection of NO is greatly desired yet remains challenging. Here we report the design and development of novel Full text Cite

Design and Characterization of Hyperpolarized 15N-BBCP as a H2O2-Sensing Probe.

Journal Article ACS sensors · October 2022 Hydrogen peroxide (H2O2) is a type of reactive oxygen species that regulates essential biological processes. Despite the central role of H2O2 in pathophysiological states, available molecular probes for assessing ... Full text Cite

Recent Advances in 1,2-Amino(hetero)arylation of Alkenes.

Journal Article Chemistry, an Asian journal · June 2022 Alkene amino(hetero)arylation presents a highly efficient and straightforward strategy for direct installation of amino groups and heteroaryl rings across a double bond simultaneously. An extensive array of practical transformations has been developed via ... Full text Cite

State-of-the-art accounts of hyperpolarized 15N-labeled molecular imaging probes for magnetic resonance spectroscopy and imaging.

Journal Article Chemical science · June 2022 Hyperpolarized isotope-labeled agents have significantly advanced nuclear magnetic resonance spectroscopy and imaging (MRS/MRI) of physicochemical activities at molecular levels. An emerging advance in this area is exciting developments of 15N-l ... Full text Cite

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes.

Journal Article Angewandte Chemie (International ed. in English) · December 2021 Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, ... Full text Cite

15N-Azides as practical and effective tags for developing long-lived hyperpolarized agents.

Journal Article Chemical science · November 2021 Azide moieties, unique linear species containing three nitrogen atoms, represent an attractive class of molecular tag for hyperpolarized magnetic resonance imaging (HP-MRI). Here we demonstrate (15N)3-azide-containing molecules exhibi ... Full text Cite

Copper-Catalyzed Aminoheteroarylation of Unactivated Alkenes through Distal Heteroaryl Migration.

Journal Article ACS catalysis · July 2021 We report a copper-catalyzed aminoheteroarylation of unactivated alkenes to access valuable heteroarylethylamine motif. The developed reaction features a copper-catalyzed intermolecular electrophilic amination of the alkenes followed by a migratory heteroa ... Full text Cite

Development of Novel 18F-PET Agents for Tumor Hypoxia Imaging.

Journal Article Journal of medicinal chemistry · May 2021 Tumor hypoxia is a major factor responsible for tumor progression, metastasis, invasion, and treatment resistance, leading to low local tumor control and recurrence after radiotherapy in cancers. Here,18F-positron emission tomography (PET) probe ... Full text Cite

Copper-Catalyzed Decarboxylative Functionalization of Conjugated β,γ-Unsaturated Carboxylic Acids.

Journal Article ACS catalysis · November 2020 Copper-catalyzed decarboxylative coupling reactions of conjugated β,γ-unsaturated carboxylic acids have been achieved for allylic amination, alkylation, sulfonylation, and phosphinoylation. This approach was effective for a broad scope of amino, alk ... Full text Cite

Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration.

Journal Article Organic letters · June 2020 Featured Publication A copper-catalyzed aminocyanation of alkenes has been achieved through distal cyano migration using O-benzoylhydroxylamines and N-fluorobenzenesulfonimides. This method offers a rapid approach to generate diverse β-amino and β-sulfonimido nit ... Full text Cite

Structure-Functional-Selectivity Relationship Studies of Novel Apomorphine Analogs to Develop D1R/D2R Biased Ligands.

Journal Article ACS medicinal chemistry letters · March 2020 Loss of dopamine neurons is central to the manifestation of Parkinson's disease motor symptoms. The dopamine precursor L-DOPA, the most commonly used therapeutic agent for Parkinson's disease, can restore normal movement yet cause side-effects such as dysk ... Full text Cite

Application of 15N2-Diazirines as a Versatile Platform for Hyperpolarization of Biological Molecules by d-DNP.

Journal Article Bioconjugate chemistry · March 2020 Featured Publication 15N2-Diazirines represent an attractive class of imaging tags for hyperpolarized magnetic resonance imaging (HP-MRI), offering desirable biocompatibility, ease of incorporation into a variety of molecules, and ability to deliver long- ... Full text Cite

1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines.

Journal Article Organic letters · February 2020 Featured Publication ortho-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, in situ nucleophilic a ... Full text Cite

Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids.

Journal Article ACS catalysis · November 2019 A three-component reaction for 1,2-amino oxygenation of 1,3-dienes has been achieved using O-acyl hydroxylamines and carboxylic acids. The reaction occurs through copper-catalyzed amination of olefins followed by nucleophilic addition of carboxylic ... Full text Cite

Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.

Journal Article The Journal of organic chemistry · February 2019 Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, ... Full text Cite

ortho-Difunctionalization of arynes by LiZnEt2(TMP)-mediated deprotonative zincation/elimination of aryl triflates

Journal Article Tetrahedron · June 28, 2018 Generation of arynes from aryl triflates has been achieved using lithium diethyl(tetramethylpiperidyl)-zincate base LiZnEt2(TMP), via a directed ortho-deprotonative zincation and subsequent elimination of the triflate group. The aryne formation has been de ... Full text Cite

Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Journal Article Angewandte Chemie (International ed. in English) · April 2018 α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C-H zincation and copper-catalyzed C(sp3 )-C(sp2 ) cross-coupling reaction using vinylphenyliodonium salts. The viny ... Full text Cite

A Novel 18 F-Labeling Method for the Synthesis of [ 18 F]-Piperidine-Containing Ligands as Potential PET Radiotracers for σ Receptors

Journal Article Synlett · March 1, 2018 We report a novel 18 F-labeling method for the preparation of 18 F-containing piperidine derivatives. This method is demonstrated on the design and synthesis of 18 F-labeled potential PET radiotracers of σ receptors for initial biological evaluations. 1 In ... Full text Cite

Celebrating the 130th anniversary of Wuhan University.

Journal Article Chemical science · February 2024 Lin Zhuang, Qiu Wang, Aiwen Lei and Qianghui Zhou introduce the Chemical Science and Green Chemistry joint themed collection celebrating the 130th Anniversary of Wuhan University. ... Full text Cite

Copper-Catalyzed Three-Component Aminofluorination of Alkenes and 1,3-Dienes: Direct Entry to Diverse β-Fluoroalkylamines.

Journal Article Journal of the American Chemical Society · November 2022 Rapid and efficient access to structurally diverse β-fluoroalkylamines is in high demand, with their wide presence and great importance in medicinal chemistry and drug development. Direct 1,2-aminofluorination of alkenes offers an ideal strategy for one-st ... Full text Cite

Design, synthesis and evaluation of 15N- and 13C-labeled molecular probes as hyperpolarized nitric oxide sensors.

Journal Article Bioorganic & medicinal chemistry · October 2022 Nitric oxide (NO) is an important signaling molecule involved in a wide range of biological processes. Development of non-invasive, real-time detection of NO is greatly desired yet remains challenging. Here we report the design and development of novel Full text Cite

Design and Characterization of Hyperpolarized 15N-BBCP as a H2O2-Sensing Probe.

Journal Article ACS sensors · October 2022 Hydrogen peroxide (H2O2) is a type of reactive oxygen species that regulates essential biological processes. Despite the central role of H2O2 in pathophysiological states, available molecular probes for assessing ... Full text Cite

Recent Advances in 1,2-Amino(hetero)arylation of Alkenes.

Journal Article Chemistry, an Asian journal · June 2022 Alkene amino(hetero)arylation presents a highly efficient and straightforward strategy for direct installation of amino groups and heteroaryl rings across a double bond simultaneously. An extensive array of practical transformations has been developed via ... Full text Cite

State-of-the-art accounts of hyperpolarized 15N-labeled molecular imaging probes for magnetic resonance spectroscopy and imaging.

Journal Article Chemical science · June 2022 Hyperpolarized isotope-labeled agents have significantly advanced nuclear magnetic resonance spectroscopy and imaging (MRS/MRI) of physicochemical activities at molecular levels. An emerging advance in this area is exciting developments of 15N-l ... Full text Cite

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes.

Journal Article Angewandte Chemie (International ed. in English) · December 2021 Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, ... Full text Cite

15N-Azides as practical and effective tags for developing long-lived hyperpolarized agents.

Journal Article Chemical science · November 2021 Azide moieties, unique linear species containing three nitrogen atoms, represent an attractive class of molecular tag for hyperpolarized magnetic resonance imaging (HP-MRI). Here we demonstrate (15N)3-azide-containing molecules exhibi ... Full text Cite

Copper-Catalyzed Aminoheteroarylation of Unactivated Alkenes through Distal Heteroaryl Migration.

Journal Article ACS catalysis · July 2021 We report a copper-catalyzed aminoheteroarylation of unactivated alkenes to access valuable heteroarylethylamine motif. The developed reaction features a copper-catalyzed intermolecular electrophilic amination of the alkenes followed by a migratory heteroa ... Full text Cite

Development of Novel 18F-PET Agents for Tumor Hypoxia Imaging.

Journal Article Journal of medicinal chemistry · May 2021 Tumor hypoxia is a major factor responsible for tumor progression, metastasis, invasion, and treatment resistance, leading to low local tumor control and recurrence after radiotherapy in cancers. Here,18F-positron emission tomography (PET) probe ... Full text Cite

Copper-Catalyzed Decarboxylative Functionalization of Conjugated β,γ-Unsaturated Carboxylic Acids.

Journal Article ACS catalysis · November 2020 Copper-catalyzed decarboxylative coupling reactions of conjugated β,γ-unsaturated carboxylic acids have been achieved for allylic amination, alkylation, sulfonylation, and phosphinoylation. This approach was effective for a broad scope of amino, alk ... Full text Cite

Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration.

Journal Article Organic letters · June 2020 Featured Publication A copper-catalyzed aminocyanation of alkenes has been achieved through distal cyano migration using O-benzoylhydroxylamines and N-fluorobenzenesulfonimides. This method offers a rapid approach to generate diverse β-amino and β-sulfonimido nit ... Full text Cite

Structure-Functional-Selectivity Relationship Studies of Novel Apomorphine Analogs to Develop D1R/D2R Biased Ligands.

Journal Article ACS medicinal chemistry letters · March 2020 Loss of dopamine neurons is central to the manifestation of Parkinson's disease motor symptoms. The dopamine precursor L-DOPA, the most commonly used therapeutic agent for Parkinson's disease, can restore normal movement yet cause side-effects such as dysk ... Full text Cite

Application of 15N2-Diazirines as a Versatile Platform for Hyperpolarization of Biological Molecules by d-DNP.

Journal Article Bioconjugate chemistry · March 2020 Featured Publication 15N2-Diazirines represent an attractive class of imaging tags for hyperpolarized magnetic resonance imaging (HP-MRI), offering desirable biocompatibility, ease of incorporation into a variety of molecules, and ability to deliver long- ... Full text Cite

1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines.

Journal Article Organic letters · February 2020 Featured Publication ortho-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, in situ nucleophilic a ... Full text Cite

Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids.

Journal Article ACS catalysis · November 2019 A three-component reaction for 1,2-amino oxygenation of 1,3-dienes has been achieved using O-acyl hydroxylamines and carboxylic acids. The reaction occurs through copper-catalyzed amination of olefins followed by nucleophilic addition of carboxylic ... Full text Cite

Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.

Journal Article The Journal of organic chemistry · February 2019 Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, ... Full text Cite

ortho-Difunctionalization of arynes by LiZnEt2(TMP)-mediated deprotonative zincation/elimination of aryl triflates

Journal Article Tetrahedron · June 28, 2018 Generation of arynes from aryl triflates has been achieved using lithium diethyl(tetramethylpiperidyl)-zincate base LiZnEt2(TMP), via a directed ortho-deprotonative zincation and subsequent elimination of the triflate group. The aryne formation has been de ... Full text Cite

Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Journal Article Angewandte Chemie (International ed. in English) · April 2018 α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C-H zincation and copper-catalyzed C(sp3 )-C(sp2 ) cross-coupling reaction using vinylphenyliodonium salts. The viny ... Full text Cite

A Novel 18 F-Labeling Method for the Synthesis of [ 18 F]-Piperidine-Containing Ligands as Potential PET Radiotracers for σ Receptors

Journal Article Synlett · March 1, 2018 We report a novel 18 F-labeling method for the preparation of 18 F-containing piperidine derivatives. This method is demonstrated on the design and synthesis of 18 F-labeled potential PET radiotracers of σ receptors for initial biological evaluations. 1 In ... Full text Cite

15N4-1,2,4,5-tetrazines as potential molecular tags: Integrating bioorthogonal chemistry with hyperpolarization and unearthing para-N2.

Journal Article Science advances · March 2018 Hyperpolarized magnetic resonance (HP-MR) is a powerful, sensitive, and noninvasive approach to visualize molecular structure, function, and dynamics in vitro and in vivo. Current applications of HP-MR mostly rely on hyperpolarization of target compounds i ... Full text Cite

Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents.

Journal Article Chemical science · December 2017 A copper-catalyzed aminoalkynylation of alkenes is achieved with ethynylbenziodoxolone (EBX) reagents under mild conditions with only 1 mol% copper catalyst. This transformation allows for rapid construction of diverse important azahetereocycles and instal ... Full text Cite

Diazirines as Potential Molecular Imaging Tags: Probing the Requirements for Efficient and Long‐Lived SABRE‐Induced Hyperpolarization

Journal Article Angewandte Chemie · September 25, 2017 AbstractDiazirines are an attractive class of potential molecular tags for magnetic resonance imaging owing to their biocompatibility and ease of incorporation into a large variety of molecules. As recently reported, Full text Cite

Diazirines as Potential Molecular Imaging Tags: Probing the Requirements for Efficient and Long-Lived SABRE-Induced Hyperpolarization.

Journal Article Angewandte Chemie (International ed. in English) · September 2017 Diazirines are an attractive class of potential molecular tags for magnetic resonance imaging owing to their biocompatibility and ease of incorporation into a large variety of molecules. As recently reported, 15 N2 -diazirine can be h ... Full text Cite

Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.

Journal Article Journal of the American Chemical Society · September 2017 A copper-catalyzed aminoazidation of unactivated alkenes is achieved for the synthesis of versatile unsymmetrical 1,2-diamine derivatives. This transformation offers an effective approach to installing an amide and an azide from two diffenent amino precurs ... Full text Cite

Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Journal Article Journal of the American Chemical Society · August 2017 Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for ... Full text Cite

Direct Hyperpolarization of Nitrogen-15 in Aqueous Media with Parahydrogen in Reversible Exchange.

Journal Article Journal of the American Chemical Society · June 2017 Signal amplification by reversible exchange (SABRE) is an inexpensive, fast, and even continuous hyperpolarization technique that uses para-hydrogen as hyperpolarization source. However, current SABRE faces a number of stumbling blocks for translation to b ... Full text Cite

Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.

Journal Article Organic letters · March 2017 Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ... Full text Cite

Generalizing, Extending, and Maximizing Nitrogen-15 Hyperpolarization Induced by Parahydrogen in Reversible Exchange.

Journal Article The journal of physical chemistry. C, Nanomaterials and interfaces · March 2017 Signal Amplification by Reversible Exchange (SABRE) is a fast and convenient NMR hyperpolarization method that uses cheap and readily available para-hydrogen as a hyperpolarization source. SABRE can hyperpolarize protons and heteronuclei. Here we fo ... Full text Cite

Emerging Developments Using Nitrogen-Heteroatom Bonds as Amination Reagents in the Synthesis of Aminoarenes.

Journal Article The Journal of organic chemistry · January 2017 Aminoarenes constitute valuable building blocks in organic synthesis and an essential skeleton ubiquitously found in ligands, agrochemicals, and pharmaceuticals. This Synopsis presents recent amination methods using nitrogen-heteroatom bonds as a powerful ... Full text Cite

Arylation, Vinylation, and Alkynylation of Electron-Deficient (Hetero)arenes Using Iodonium Salts.

Journal Article Organic letters · October 2016 Arylation, vinylation, and alkynylation of electron-deficient arenes and heteroarenes have been achieved by chemoselective C-H zincation followed by copper-catalyzed coupling reactions using iodonium salts. This approach offers a direct and general access ... Full text Cite

Copper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using O-Benzoylhydroxylamines.

Journal Article Journal of the American Chemical Society · May 2016 A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate scop ... Full text Cite

Direct and cost-efficient hyperpolarization of long-lived nuclear spin states on universal 15N2-diazirine molecular tags

Journal Article Science Advances · March 25, 2016 Conventional magnetic resonance (MR) faces serious sensitivity limitations which can be overcome by hyperpolarization methods, but the most common method (dynamic nuclear polarization) is complex and expensive, and applications are limited by short spin li ... Full text Open Access Link to item Cite

Copper-catalyzed aminotrifluoromethylation of alkenes: A facile synthesis of CF3-containing lactams

Journal Article Organic Chemistry Frontiers · February 1, 2016 Copper-catalyzed aminotrifluoromethylation of alkenes using amides as nucleophiles has been developed. It provides a rapid and efficient access to a variety of CF3-containing lactams. The reaction proceeds under mild conditions with a good scope and functi ... Full text Cite

Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines.

Journal Article Beilstein journal of organic chemistry · January 2016 This paper reports a novel approach for the direct and facile synthesis of 1,2-oxyamino moieties via an intermolecular copper-catalyzed oxyamination of olefins. This strategy utilizes O-benzoylhydroxylamines as an electrophilic amine source and carboxylic ... Full text Cite

Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones.

Journal Article Organic letters · December 2015 A novel approach toward the synthesis of sterically hindered o-aminophenols has been achieved by a formal aryne insertion into hydroxyindolinones. This transformation offers a rapid and efficient entry to diverse o-aminophenol scaffolds under mild transiti ... Full text Cite

Copper-catalyzed diamination of unactivated alkenes with hydroxylamines.

Journal Article Chemical science · July 2015 A copper-catalyzed regio- and stereoselective diamination of unactivated alkenes has been developed with O-acylhydroxylamines as electrophilic nitrogen sources and oxidants. This method provides the first example of metal-catalyzed alkene diaminatio ... Full text Cite

Synthesis of ortho-haloaminoarenes by aryne insertion of nitrogen-halide bonds.

Journal Article The Journal of organic chemistry · January 2015 A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltrifla ... Full text Cite

Copper-Catalyzed Electrophilic Amination of Heteroaromatic and Aromatic C-H Bonds via TMPZnCl•LiCl Mediated Metalation.

Journal Article Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · January 2015 Full text Cite

α-Amination of Phosphonates: A Direct Synthesis of α-Amino Phosphonic Acids and Their Derivatives

Journal Article Synlett · July 9, 2014 A direct approach to access important α-amino phosphonic acids and their derivatives through the formation of C-N bonds is described. Several α-amination reactions of phosphonates that involve electrophilic aminating agents are reviewed. A recent developme ... Full text Cite

Epithelial-to-mesenchymal transition activates PERK-eIF2α and sensitizes cells to endoplasmic reticulum stress.

Journal Article Cancer discovery · June 2014 UnlabelledEpithelial-to-mesenchymal transition (EMT) promotes both tumor progression and drug resistance, yet few vulnerabilities of this state have been identified. Using selective small molecules as cellular probes, we show that induction of EMT ... Full text Cite

Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.

Journal Article Angewandte Chemie (International ed. in English) · April 2014 Direct amination of heteroarenes and arenes has been achieved in a one-pot CH zincation/copper-catalyzed electrophilic amination procedure. This amination method provides an efficient and rapid approach to access a diverse range of heteroaromatic and arom ... Full text Cite

Microtubule acetylation amplifies p38 kinase signalling and anti-inflammatory IL-10 production.

Journal Article Nat Commun · March 17, 2014 Reversible acetylation of α-tubulin is an evolutionarily conserved modification in microtubule networks. Despite its prevalence, the physiological function and regulation of microtubule acetylation remain poorly understood. Here we report that macrophages ... Full text Link to item Cite

Selective α-amination and α-acylation of esters and amides via dual reactivity of O-acylhydroxylamines toward zinc enolates.

Journal Article Chemical communications (Cambridge, England) · March 2014 Selective α-amination and α-acylation of esters and amides have been developed, employing O-acylhydroxylamines as a dually reactive aminating and acylating reagent. Treatment of zinc enolates with O-acylhydroxylamines provides solely 1,3-dicarbonyl compoun ... Full text Cite

Copper-catalyzed α-amination of phosphonates and phosphine oxides: a direct approach to α-amino phosphonic acids and derivatives.

Journal Article Angewandte Chemie (International ed. in English) · February 2014 A direct approach to important α-amino phosphonic acids and its derivatives has been developed by using copper-catalyzed electrophilic amination of α-phosphonate zincates with O-acyl hydroxylamines. This amination provides the first example of CN bond for ... Full text Cite

One-pot synthesis of 3-azido- and 3-aminopiperidines by intramolecular cyclization of unsaturated amines.

Journal Article The Journal of organic chemistry · January 2014 A highly efficient one-pot synthesis of 3-azidopiperidines has been achieved by an intramolecular cyclization of unsaturated amines that allows for the nucleophilic installation of an azide moiety. This method unlocks the versatile employment of the azide ... Full text Cite

Storage of hydrogen spin polarization in long-lived 13C2 singlet order and implications for hyperpolarized magnetic resonance imaging.

Journal Article J Am Chem Soc · July 3, 2013 Hyperpolarized magnetic resonance imaging (MRI) is a powerful technique enabling real-time monitoring of metabolites at concentration levels not accessible by standard MRI techniques. A considerable challenge this technique faces is the T1 decay of the hyp ... Full text Link to item Cite

Insertion of arynes into N-halo bonds: a direct approach to o-haloaminoarenes.

Journal Article Organic letters · July 2013 A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high ... Full text Cite

Gossypol and an HMT G9a inhibitor act in synergy to induce cell death in pancreatic cancer cells.

Journal Article Cell death & disease · June 2013 The histone methyltransferase G9a is overexpressed in a variety of cancer types, including pancreatic adenocarcinoma, and promotes tumor invasiveness and metastasis. We recently reported the discovery of BRD4770, a small-molecule inhibitor of G9a that indu ... Full text Cite

An efficient synthesis of fluorinated azaheterocycles by aminocyclization of alkenes.

Journal Article Organic letters · April 2013 A general and efficient approach to important fluorinated azaheterocycles has been developed by incorporating nucleophilic fluorination into alkene difunctionalization. This intramolecular aminofluorination transformation of alkenes has been achieved via t ... Full text Cite

A small-molecule probe of the histone methyltransferase G9a induces cellular senescence in pancreatic adenocarcinoma.

Journal Article ACS chemical biology · July 2012 Post-translational modifications of histones alter chromatin structure and play key roles in gene expression and specification of cell states. Small molecules that target chromatin-modifying enzymes selectively are useful as probes and have promise as ther ... Full text Cite

A novel HDAC inhibitor with a hydroxy-pyrimidine scaffold.

Journal Article Bioorganic & medicinal chemistry letters · July 2011 Histone deacetylases (HDACs) are enzymes involved in many important biological functions. They have been linked to a variety of cancers, psychiatric disorders, and other diseases. Since small molecules can serve as probes to study the relevant biological r ... Full text Cite

Copper-mediated amidation of heterocyclic and aromatic C-H bonds.

Journal Article Organic letters · November 2009 A copper-mediated aerobic coupling reaction enables direct amidation of heterocycles or aromatics having weakly acidic C-H bonds with a variety of nitrogen nucleophiles. These reactions provide efficient access to many biologically important skeletons, inc ... Full text Cite

Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.

Journal Article The Journal of organic chemistry · September 2006 Several 2-imido substituted furans were found to undergo a rapid intramolecular [4 + 2]-cycloaddition to deliver oxabicyclo adducts in good to excellent yields. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, it was possible to ... Full text Cite

Rhodium(I)-catalyzed nucleophilic ring-opening reactions of oxabicyclo adducts derived from the [4 + 2]-cycloaddition of 2-imido-substituted furans.

Journal Article The Journal of organic chemistry · April 2006 A series of 2-imido-substituted furans containing tethered unsaturation were prepared by the addition of the lithium carbamate of furan-2-ylcarbamic acid tert-butyl ester to a solution of the mixed anhydride of an appropriately substituted 3-butenoic acid. ... Full text Cite

Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

Journal Article Organic letters · February 2006 [reaction: see text] A new strategy for the synthesis of 3-demethoxyerythratidinone has been developed and is based on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. During the course of the synthesis, several ... Full text Cite

Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles

Journal Article Tetrahedron Letters · January 23, 2006 The additive Pummerer reaction of several heteroaromatic sulfilimines has been investigated. The overall process involves the reaction of the sulfilimine with TFAA to produce a transient N-tosyl-N-trifluoroacetyl sulfonium ion. Nucleophilic attack at the a ... Full text Cite

Dichloroketene-induced cyclizations of vinyl sulfilimines: application of the method in the synthesis of (+/-)-desoxyeseroline.

Journal Article The Journal of organic chemistry · October 2005 The reactions of several aryl-, furanyl-, and vinyl-substituted sulfilimines with dichloroketene proceeded at 25 degrees C to yield thioalkyl-substituted gamma-lactams. The overall process involves nucleophilic addition of the nitrogen atom of the sulfilim ... Full text Cite

A new synthesis of gamma-lactams based on the reaction of vinyl sulfilimines with dichloroketene.

Journal Article Organic letters · March 2005 The reactions of several aryl-, furanyl-, and vinyl substituted sulfilimines with dichloroketene proceeded at 25 degrees C to yield thioalkyl substituted gamma-lactams which, in turn, were converted to a variety of nitrogen-containing substrates. [reaction ... Full text Cite

Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.

Journal Article Organic letters · June 2004 [reaction: see text] A new strategy for epi-zephyranthine has been developed that is based in part on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. By using a Rh(I)-catalyzed ring opening of the resulting oxa ... Full text Cite

A new strategy toward indole alkaloids involving an intramolecular cycloaddition/rearrangement cascade.

Journal Article The Journal of organic chemistry · May 2004 The intramolecular Diels-Alder reaction between an amidofuran moiety tethered onto an indole component was examined as a strategy for the synthesis of Aspidosperma alkaloids. Furanyl carbamate 23 was acylated using the mixed anhydride 26 to provide amidofu ... Full text Cite

Tandem Pummerer/Mannich Cyclization Cascade of α‐Sulfinylamides as a Method to Prepare Aza‐Heterocycles.

Journal Article ChemInform · January 28, 2003 AbstractFor Abstract see ChemInform Abstract in Full Text. ... Full text Cite

Tandem Pummerer/Mannich cyclization cascade of alpha-sulfinylamides as a method to prepare aza-heterocycles.

Journal Article The Journal of organic chemistry · August 2002 A series of alpha-sulfinylenamides was conveniently prepared by the condensation of a primary amine with a ketone, followed by reaction of the resulting imine with ethylsulfenylacetyl chloride and subsequent oxidation with sodium periodate. When treated wi ... Full text Cite