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 (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Hemric, BN; Chen, AW; Wang, Q

Published Date

  • November 2019

Published In

Volume / Issue

  • 9 / 11

Start / End Page

  • 10070 - 10076

PubMed ID

  • 31692984

Pubmed Central ID

  • PMC6830571

Electronic International Standard Serial Number (EISSN)

  • 2155-5435

International Standard Serial Number (ISSN)

  • 2155-5435

Digital Object Identifier (DOI)

  • 10.1021/acscatal.9b03076


  • eng