Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation

Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation

An ortho-alkenylation reaction of an aromatic aldimine with an internal alkyne is efficiently promoted by a cobalt catalyst generated from CoBr2, triarylphosphine, and iPrMgBr. The reaction takes place under mild room-temperature conditions to afford, upon acidic hydrolysis, a variety of ortho-alken...

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Main Authors: Yamakawa, Takeshi, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/99588
http://hdl.handle.net/10220/17467
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-995882020-03-07T12:34:48Z Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation Yamakawa, Takeshi Yoshikai, Naohiko School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry An ortho-alkenylation reaction of an aromatic aldimine with an internal alkyne is efficiently promoted by a cobalt catalyst generated from CoBr2, triarylphosphine, and iPrMgBr. The reaction takes place under mild room-temperature conditions to afford, upon acidic hydrolysis, a variety of ortho-alkenylated aromatic aldehydes in moderate to excellent yields. The neighboring formyl and alkenyl groups in the product can be utilized as synthetic handles for the facile construction of indene and naphthalene carbocycles. 2013-11-08T06:00:56Z 2019-12-06T20:09:17Z 2013-11-08T06:00:56Z 2019-12-06T20:09:17Z 2013 2013 Journal Article Yamakawa, T., & Yoshikai, N. (2013). Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation. Tetrahedron, 69(22), 4459-4465 0040-4020 https://hdl.handle.net/10356/99588 http://hdl.handle.net/10220/17467 10.1016/j.tet.2013.02.092 en Tetrahedron
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Yamakawa, Takeshi
Yoshikai, Naohiko
Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation
description An ortho-alkenylation reaction of an aromatic aldimine with an internal alkyne is efficiently promoted by a cobalt catalyst generated from CoBr2, triarylphosphine, and iPrMgBr. The reaction takes place under mild room-temperature conditions to afford, upon acidic hydrolysis, a variety of ortho-alkenylated aromatic aldehydes in moderate to excellent yields. The neighboring formyl and alkenyl groups in the product can be utilized as synthetic handles for the facile construction of indene and naphthalene carbocycles.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Yamakawa, Takeshi
Yoshikai, Naohiko
format Article
author Yamakawa, Takeshi
Yoshikai, Naohiko
author_sort Yamakawa, Takeshi
title Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation
title_short Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation
title_full Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation
title_fullStr Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation
title_full_unstemmed Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C–H bond activation
title_sort cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted c–h bond activation
publishDate 2013
url https://hdl.handle.net/10356/99588
http://hdl.handle.net/10220/17467
_version_ 1681045860169809920

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