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Title: Cobalt-Catalyzed Arylative Cyclization of Acetylenic Esters and Ketones with Arylzinc Reagents through 1,4-Cobalt Migration
Authors: Yan, Jianming
Yoshikai, Naohiko
Keywords: Cobalt
Organozinc reagents
Issue Date: 2016
Source: Yan, J., & Yoshikai, N. (2016). Cobalt-Catalyzed Arylative Cyclization of Acetylenic Esters and Ketones with Arylzinc Reagents through 1,4-Cobalt Migration. ACS Catalysis, 6(6), 3738-3742.
Series/Report no.: ACS Catalysis
Abstract: 1,4-Migrations of organopalladium and organorhodium species have been utilized for the development of various cascade reactions involving remote C–H bond activation. Recently, we reported a cobalt-catalyzed migratory arylzincation reaction of an alkyne that features alkenyl-to-aryl 1,4-cobalt migration and cobalt-to-zinc transmetalation as key steps. We report herein that the cobalt/arylzinc combination can also promote a cascade arylative cyclization reaction of alkynes bearing pendant ester or ketone moieties to afford benzo-fused cyclic ketone or alcohol products, respectively. The reaction is considered to proceed through insertion of the alkyne into an arylcobalt species, 1,4-cobalt migration, and intramolecular organocobalt addition to the carbonyl group. The present cobalt/arylzinc system may not only serve as an alternative to previously reported rhodium/arylboron and iridium/arylboron systems but also complement their scopes in the arylative cyclization.
DOI: 10.1021/acscatal.6b01039
Schools: School of Physical and Mathematical Sciences 
Rights: © 2016 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by ACS Catalysis, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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