Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer

Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer

A cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling reaction between an aryl imine and a 2-bromobenzyl-protected secondary amine is reported. Promoted by a combination of a cobalt–N-heterocyclic carbene catalyst and a Grignard reagent, the reaction allows for the introduction of α-aminoalkyl groups into t...

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Main Authors: Sun, Qiao, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2019
Subjects:
Catalyst
DRNTU::Science::Chemistry
Hydrogen Atom Transfer
Online Access:https://hdl.handle.net/10356/90289
http://hdl.handle.net/10220/48486
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-902892023-02-28T19:37:05Z Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer Sun, Qiao Yoshikai, Naohiko School of Physical and Mathematical Sciences Catalyst DRNTU::Science::Chemistry Hydrogen Atom Transfer A cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling reaction between an aryl imine and a 2-bromobenzyl-protected secondary amine is reported. Promoted by a combination of a cobalt–N-heterocyclic carbene catalyst and a Grignard reagent, the reaction allows for the introduction of α-aminoalkyl groups into the ortho position of the imine at a mild temperature. The cobalt catalyst is proposed to play key roles in two distinct modes of C–H cleavage, i.e., directed C–H metalation and 1,5-hydrogen atom transfer (HAT). MOE (Min. of Education, S’pore) Accepted version 2019-05-30T04:47:25Z 2019-12-06T17:44:54Z 2019-05-30T04:47:25Z 2019-12-06T17:44:54Z 2017 Journal Article Sun, Q., & Yoshikai, N. (2018). Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer. Organic Chemistry Frontiers, 5(4), 582-585. doi:10.1039/C7QO00906B 2052-4110 https://hdl.handle.net/10356/90289 http://hdl.handle.net/10220/48486 10.1039/C7QO00906B en Organic Chemistry Frontiers © 2018 the Partner Organisations. All rights reserved. This paper was published in Organic Chemistry Frontiers and is made available with permission of the Partner Organisations. 5 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 Catalyst
DRNTU::Science::Chemistry
Hydrogen Atom Transfer
spellingShingle Catalyst
DRNTU::Science::Chemistry
Hydrogen Atom Transfer
Sun, Qiao
Yoshikai, Naohiko
Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer
description A cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling reaction between an aryl imine and a 2-bromobenzyl-protected secondary amine is reported. Promoted by a combination of a cobalt–N-heterocyclic carbene catalyst and a Grignard reagent, the reaction allows for the introduction of α-aminoalkyl groups into the ortho position of the imine at a mild temperature. The cobalt catalyst is proposed to play key roles in two distinct modes of C–H cleavage, i.e., directed C–H metalation and 1,5-hydrogen atom transfer (HAT).
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Sun, Qiao
Yoshikai, Naohiko
format Article
author Sun, Qiao
Yoshikai, Naohiko
author_sort Sun, Qiao
title Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer
title_short Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer
title_full Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer
title_fullStr Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer
title_full_unstemmed Cobalt-catalyzed C(sp2)–H/C(sp3)–H coupling via directed C–H activation and 1,5-hydrogen atom transfer
title_sort cobalt-catalyzed c(sp2)–h/c(sp3)–h coupling via directed c–h activation and 1,5-hydrogen atom transfer
publishDate 2019
url https://hdl.handle.net/10356/90289
http://hdl.handle.net/10220/48486
_version_ 1759853097447849984

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