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Org Lett. 2015 Mar 6;17(5):1332-5. doi: 10.1021/acs.orglett.5b00340. Epub 2015 Feb 25.

An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation.

Author information

1
Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.

Abstract

The development of a method for the Rh(III)-catalyzed direct vinylation of an aromatic C-H bond to give functionalized styrenes in good yield, using vinyl acetate as a convenient and inexpensive vinyl source, is reported. High functional group tolerance is demonstrated for electronically distinct arenes as well as different directing groups. Mechanistic investigation resulted in the characterization of a novel rhodium-metallacycle, which represents the first X-ray structure of a [1,2]-Rh(III)-alkenyl addition adduct.

PMID:
25715077
PMCID:
PMC4446975
DOI:
10.1021/acs.orglett.5b00340
[Indexed for MEDLINE]
Free PMC Article

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