Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation

Qiao Sun; Naohiko Yoshikai

doi:10.1021/acs.orglett.9b01846

Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation

Qiao Sun, Naohiko Yoshikai

PHA - Molecular Pharmaceutical Science

Nanyang Technological University

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

16 Citations (Scopus)

Abstract

A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine derivatives in moderate to good yields. The reaction tolerates a variety of substituents on the aryl imine as well as various modifications on the bromo-alkene substrate.

Original language	English
Pages (from-to)	5238-5242
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.9b01846
Publication status	Published - 2019 Jun 20

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title = "Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation",

abstract = "A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine derivatives in moderate to good yields. The reaction tolerates a variety of substituents on the aryl imine as well as various modifications on the bromo-alkene substrate.",

author = "Qiao Sun and Naohiko Yoshikai",

note = "Funding Information: This work was supported by Nanyang Technological University and Singapore Ministry of Education (MOE2016-T2-2-043). Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Yoshikai, Naohiko

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N2 - A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine derivatives in moderate to good yields. The reaction tolerates a variety of substituents on the aryl imine as well as various modifications on the bromo-alkene substrate.

AB - A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine derivatives in moderate to good yields. The reaction tolerates a variety of substituents on the aryl imine as well as various modifications on the bromo-alkene substrate.

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Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation

Abstract

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