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 α-sp3 hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C–C bond cleavage to give the corresponding carbonitri...

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Bibliographic Details
Main Authors: Ya Lin Tnay, Gim Yean Ang, Shunsuke Chiba
Format: Article
Language:English
Published: Beilstein-Institut 2015-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
C–C bond cleavage
copper
ketimines
molecular oxygen
radical
Online Access:https://doi.org/10.3762/bjoc.11.209
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spelling doaj-5266b2164f374353a94871a502eb88062021-03-02T10:12:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-10-011111933194310.3762/bjoc.11.2091860-5397-11-209Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketiminesYa Lin Tnay0Gim Yean Ang1Shunsuke Chiba2Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, SingaporeDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, SingaporeDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, SingaporeWe report herein studies on copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines. Treatment of N–H ketimines having an α-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.https://doi.org/10.3762/bjoc.11.209C–C bond cleavagecopperketiminesmolecular oxygenradical
collection DOAJ
language English
format Article
sources DOAJ
author Ya Lin Tnay
Gim Yean Ang
Shunsuke Chiba
spellingShingle Ya Lin Tnay
Gim Yean Ang
Shunsuke Chiba
Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
Beilstein Journal of Organic Chemistry
C–C bond cleavage
copper
ketimines
molecular oxygen
radical
author_facet Ya Lin Tnay
Gim Yean Ang
Shunsuke Chiba
author_sort Ya Lin Tnay
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
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2015-10-01
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 α-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.
topic C–C bond cleavage
copper
ketimines
molecular oxygen
radical
url https://doi.org/10.3762/bjoc.11.209
work_keys_str_mv AT yalintnay coppercatalyzedaerobicradicalccbondcleavageofnhketimines
AT gimyeanang coppercatalyzedaerobicradicalccbondcleavageofnhketimines
AT shunsukechiba coppercatalyzedaerobicradicalccbondcleavageofnhketimines
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