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HERO ID
7202503
Reference Type
Journal Article
Title
Doubly Regioselective C-H Hydroarylation of Unsymmetrical Alkynes Using Carboxylates as Deciduous Directing Groups
Author(s)
Biafora, A; Khan, BA; Bahri, J; Hewer, JM; Goossen, LJ; ,
Year
2017
Is Peer Reviewed?
1
Journal
Organic Letters
ISSN:
1523-7060
EISSN:
1523-7052
Language
English
PMID
28195735
DOI
10.1021/acs.orglett.7b00300
Abstract
A catalyst system composed of [(C6Me6)RuCl2]2, potassium carbonate/guanidine carbonate, and mesitoic acid efficiently promotes the doubly regioselective C-H hydroarylation of unsymmetrical alkynes. The process involves carboxylate-directed ortho-C-H bond activation followed by regioselective addition to the alkyne C-C triple bond with concerted decarboxylation. This action of the carboxylate as a deciduous directing group ensures exclusive monovinylation with high selectivity for the (E)-1,2-diarylalkene.
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