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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.

Publication ,  Journal Article
Hemric, BN; Chen, AW; Wang, Q
Published in: 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 acids, offering high levels of chemo-, regio-, and site-selectivity. The method is effective for both terminal and internal 1,3-dienes, including those bearing multiple, unsymmetrical substituents. The amino oxygenation conditions also exhibited remarkable selectivity toward 1,3-dienes over alkenes, good tolerance of sensitive functional groups, and reliable scalability.

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Published In

ACS catalysis

DOI

EISSN

2155-5435

ISSN

2155-5435

Publication Date

November 2019

Volume

9

Issue

11

Start / End Page

10070 / 10076

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry
 

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Hemric, B. N., Chen, A. W., & Wang, Q. (2019). 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. ACS Catalysis, 9(11), 10070–10076. https://doi.org/10.1021/acscatal.9b03076
Hemric, Brett N., Andy W. Chen, and Qiu Wang. “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.ACS Catalysis 9, no. 11 (November 2019): 10070–76. https://doi.org/10.1021/acscatal.9b03076.
Hemric, Brett N., et al. “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.ACS Catalysis, vol. 9, no. 11, Nov. 2019, pp. 10070–76. Epmc, doi:10.1021/acscatal.9b03076.
Journal cover image

Published In

ACS catalysis

DOI

EISSN

2155-5435

ISSN

2155-5435

Publication Date

November 2019

Volume

9

Issue

11

Start / End Page

10070 / 10076

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry