Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines

Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines

We report herein studies on copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines. Treatment of N-H ketimines having an alpha-sp3 hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C-C bond cleavage to give the corresponding carbon...

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Bibliographic Details
Main Authors: Tnay, Ya Lin, Ang, Gim Yean, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2016
Subjects:
copper
ketimines
molecular oxygen
radical
C-C bond cleavage
Online Access:https://hdl.handle.net/10356/81491
http://hdl.handle.net/10220/40822
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Institution: Nanyang Technological University
Language: English
Description
Summary:We report herein studies on copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines. Treatment of N-H ketimines having an alpha-sp3 hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C-C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalonitrile as a CN source.

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