Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.
Journal Article (Journal Article)
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, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.
Full Text
Duke Authors
Cited Authors
- Hemric, BN; Chen, AW; Wang, Q
Published Date
- February 2019
Published In
Volume / Issue
- 84 / 3
Start / End Page
- 1468 - 1488
PubMed ID
- 30588808
Pubmed Central ID
- 30588808
Electronic International Standard Serial Number (EISSN)
- 1520-6904
International Standard Serial Number (ISSN)
- 0022-3263
Digital Object Identifier (DOI)
- 10.1021/acs.joc.8b02885
Language
- eng