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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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
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spelling sg-ntu-dr.10356-814912023-02-28T19:29:31Z Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines Tnay, Ya Lin Ang, Gim Yean Chiba, Shunsuke School of Physical and Mathematical Sciences copper ketimines molecular oxygen radical C-C bond cleavage 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. Published version 2016-06-28T08:59:03Z 2019-12-06T14:32:09Z 2016-06-28T08:59:03Z 2019-12-06T14:32:09Z 2015 Journal Article Tnay, Y. L., Ang, G. Y., & Chiba, S. (2015). Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines. Beilstein Journal of Organic Chemistry, 11, 1933-1943. 1860-5397 https://hdl.handle.net/10356/81491 http://hdl.handle.net/10220/40822 10.3762/bjoc.11.209 26664613 en Beilstein Journal of Organic Chemistry © 2015 The Author(s) (Published by Beilstein-Institut). This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 11 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic copper
ketimines
molecular oxygen
radical
C-C bond cleavage
spellingShingle copper
ketimines
molecular oxygen
radical
C-C bond cleavage
Tnay, Ya Lin
Ang, Gim Yean
Chiba, Shunsuke
Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Tnay, Ya Lin
Ang, Gim Yean
Chiba, Shunsuke
format Article
author Tnay, Ya Lin
Ang, Gim Yean
Chiba, Shunsuke
author_sort Tnay, Ya Lin
title Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
title_short Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
title_full Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
title_fullStr Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
title_full_unstemmed Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
title_sort copper-catalyzed aerobic radical c-c bond cleavage of n-h ketimines
publishDate 2016
url https://hdl.handle.net/10356/81491
http://hdl.handle.net/10220/40822
_version_ 1759856909120176128

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