Journal ArticleOrganic letters · November 2024
We herein report a copper-catalyzed 1,3-aminocyclization of cyclopropanes as a direct and versatile entry into important heterocycles. This reaction was initiated by a copper-catalyzed, NFSI-promoted ring opening of cyclopropanes, followed by nucleophilic ...
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Journal ArticleChem Catalysis · March 21, 2024
In this issue of Chem Catalysis, Wang and co-workers have established an efficient and practical route for constructing versatile di-, tri-, and tetra-substituted phosphoryl allenes via a nickel-catalyzed propargylic substitution reaction, offering a power ...
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Journal ArticleChemical 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. ...
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Journal ArticleChem Catalysis · January 1, 2024
We report a copper-catalyzed 1,4-selective aminooxygenation of 1,3-dienes as a direct entry to 1,4-allylic amino alcohols. The reactions are effective on a diverse range of amide-, urea-, and ester-containing 1,3-dienes, allowing for the facile installatio ...
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Journal ArticleJournal 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 ...
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Journal ArticleBioorganic & 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
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Journal ArticleACS 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 ...
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Journal ArticleChemistry, 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 ...
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Journal ArticleChemical 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 ...
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Journal ArticleAngewandte 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, ...
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Journal ArticleChemical 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 ...
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Journal ArticleACS 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 ...
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Journal ArticleJournal 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 ...
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Journal ArticleACS 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleACS 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 ...
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Journal ArticleBioconjugate 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- ...
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Journal ArticleOrganic 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 ...
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Journal ArticleACS 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 ...
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Journal ArticleThe 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, ...
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Journal ArticleTetrahedron · 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 ...
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Journal ArticleAngewandte 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 ...
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Journal ArticleSynlett · 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 ...
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Journal ArticleScience 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 ...
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Journal ArticleChemical 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 ...
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Journal ArticleAngewandte 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,
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Journal ArticleAngewandte 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 ...
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Journal ArticleJournal 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 ...
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Journal ArticleJournal 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 ...
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Journal ArticleJournal 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleThe 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 ...
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Journal ArticleThe 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleJournal 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 ...
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Journal ArticleScience 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleBeilstein 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleChemical 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 ...
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Journal ArticleThe 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 ...
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Journal ArticleSynlett · 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 ...
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Journal ArticleCancer 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 ...
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Journal ArticleAngewandte Chemie (International ed. in English) · April 2014
Direct amination of heteroarenes and arenes has been achieved in a one-pot CH zincation/copper-catalyzed electrophilic amination procedure. This amination method provides an efficient and rapid approach to access a diverse range of heteroaromatic and arom ...
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Journal ArticleNat 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 ...
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Journal ArticleChemical 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 ...
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Journal ArticleAngewandte 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 CN bond for ...
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Journal ArticleThe 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 ...
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Journal ArticleJ 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleCell 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleACS 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 ...
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Journal ArticleBioorganic & 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleThe 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 ...
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Journal ArticleThe 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. ...
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Journal ArticleOrganic 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 ...
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Journal ArticleTetrahedron 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 ...
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Journal ArticleThe 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleOrganic 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 ...
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Journal ArticleThe 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 ...
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Journal ArticleThe 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 ...
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