Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides

A cobalt–N-heterocyclic carbene catalyst allows ortho-alkylation of aromatic imines with unactivated primary and secondary alkyl chlorides and bromides under room-temperature conditions. The scope of the reaction encompasses or complements that of cobalt-catalyzed ortho-alkylation reactions with ole...

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Main Authors: Yoshikai, Naohiko, Gao, Ke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
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Online Access:https://hdl.handle.net/10356/105074
http://hdl.handle.net/10220/20375
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spelling sg-ntu-dr.10356-1050742023-02-28T19:45:29Z Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides Yoshikai, Naohiko Gao, Ke School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry A cobalt–N-heterocyclic carbene catalyst allows ortho-alkylation of aromatic imines with unactivated primary and secondary alkyl chlorides and bromides under room-temperature conditions. The scope of the reaction encompasses or complements that of cobalt-catalyzed ortho-alkylation reactions with olefins as alkylating agents that we developed previously. Stereochemical outcomes of secondary alkylation reactions suggest that the reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing group and the cycloalkyl groups. Published version 2014-08-21T07:04:02Z 2019-12-06T21:45:41Z 2014-08-21T07:04:02Z 2019-12-06T21:45:41Z 2014 2014 Journal Article Yoshikai, N., & Gao, K. (2014). Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides. Pure and Applied Chemistry, 86(3), 419–424. 0033-4545 https://hdl.handle.net/10356/105074 http://hdl.handle.net/10220/20375 10.1515/pac-2014-5005 en Pure and applied chemistry © 2014 IUPAC & De Gruyter. This paper was published in Pure and Applied Chemistry and is made available as an electronic reprint (preprint) with permission of IUPAC & De Gruyter. The paper can be found at the following official DOI: [http://dx.doi.org/10.1515/pac-2014-5005].  One print or electronic copy may be made for personal use only. Systematic or multiple reproduction, distribution to multiple locations via electronic or other means, duplication of any material in this paper for a fee or for commercial purposes, or modification of the content of the paper is prohibited and is subject to penalties under law. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Yoshikai, Naohiko
Gao, Ke
Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides
description A cobalt–N-heterocyclic carbene catalyst allows ortho-alkylation of aromatic imines with unactivated primary and secondary alkyl chlorides and bromides under room-temperature conditions. The scope of the reaction encompasses or complements that of cobalt-catalyzed ortho-alkylation reactions with olefins as alkylating agents that we developed previously. Stereochemical outcomes of secondary alkylation reactions suggest that the reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing group and the cycloalkyl groups.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Yoshikai, Naohiko
Gao, Ke
format Article
author Yoshikai, Naohiko
Gao, Ke
author_sort Yoshikai, Naohiko
title Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides
title_short Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides
title_full Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides
title_fullStr Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides
title_full_unstemmed Cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides
title_sort cobalt-catalyzed directed alkylation of arenes with primary and secondary alkyl halides
publishDate 2014
url https://hdl.handle.net/10356/105074
http://hdl.handle.net/10220/20375
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