Coupling Reaction of Cu-Based Carbene and Nitroso Radical: A Tandem Reaction To Construct Isoxazolines

In this letter, an unprecedented cross-coupling reaction between copper carbene and nitroso radical has been developed. This radical-carbene coupling reaction (RCC reaction) offers a novel approach for the preparation of various isoxazolines, which features the construction of C–C, C–O, and CN bond...

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Published inOrganic letters Vol. 19; no. 21; pp. 5896 - 5899
Main Authors Chen, Rongxiang, Zhao, Yanwei, Fang, Shangwen, Long, Wenhao, Sun, Hongmei, Wan, Xiaobing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.11.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
H FUNCTIONALIZATION
FACILE SYNTHESIS
GAMMA-AMINO KETONES
DIRECT CONVERSION
BOND FORMATION
DIAZO-COMPOUNDS
BETA-HYDROXY KETONES
TERT-BUTYL NITRITE
CO(II)-BASED METALLORADICAL CATALYSIS
UNACTIVATED ALKENES
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Summary:In this letter, an unprecedented cross-coupling reaction between copper carbene and nitroso radical has been developed. This radical-carbene coupling reaction (RCC reaction) offers a novel approach for the preparation of various isoxazolines, which features the construction of C–C, C–O, and CN bonds in a one-pot process. The synthetic utility of our method is further enhanced by its mild reaction conditions, wide substrate scope, and simple procedures.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02885