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

Ya Lin Tnay; Gim Yean Ang; Shunsuke Chiba

doi:10.3762/bjoc.11.209

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

Ya Lin Tnay, Gim Yean Ang, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1933-1943
Number of pages	11
Journal	Beilstein Journal of Organic Chemistry
Volume	11
DOIs	https://doi.org/10.3762/bjoc.11.209
Publication status	Published - Oct 19 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 Tnay et al; licensee Beilstein-Institut.

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

C-C bond cleavage
Copper
Ketimines
Molecular oxygen
Radical

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10.3762/bjoc.11.209

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abstract = "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.",

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AU - Tnay, Ya Lin

AU - Ang, Gim Yean

AU - Chiba, Shunsuke

PY - 2015/10/19

Y1 - 2015/10/19

N2 - 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.

AB - 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.

KW - C-C bond cleavage

KW - Copper

KW - Ketimines

KW - Molecular oxygen

KW - Radical

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SN - 1860-5397

VL - 11

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EP - 1943

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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