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

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...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 3; pp. 1468 - 1488
Main Authors Hemric, Brett N, Chen, Andy W, Wang, Qiu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENTRY
DIAMINATION
ELECTROPHILIC AMINATION
OLEFINS
OXYAMINATION
UNACTIVATED ALKENES
AMINOHYDROXYLATION
AMINOOXYGENATION
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Summary: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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02885