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Palladium-Catalyzed α-Arylation of Esters with Chloroarenes

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Takuo Hama and John F. Hartwig*

Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, and Department of Chemistry, University of Illinois Urbana-Champaign, Box 58-6, Urbana, Illinois 61801

Org. Lett., 2008, 10 (8), pp 1549–1552

DOI: 10.1021/ol800258u

Publication Date (Web): March 22, 2008

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Palladium-catalyzed α-arylations of esters with chloroarenes are reported. The reactions of chloroarenes with the sodium enolates of tert-butyl propionate and methyl isobutyrate occur in high yields with 0.2−1 mol % of {[P(t-Bu)₃]PdBr}₂ or the combination of Pd(dba)₂ and P(t-Bu)₃ as catalyst. The reactions of chloroarenes with the Reformatsky reagent of tert-butyl acetate were most challenging but occurred in high yields for chlorobenzene and electron-poor chloroarenes catalyzed by 1 mol % of Pd(dba)₂ and pentaphenylferrocenyl di-tert-butylphosphine (Q-phos).

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History

Published In Issue April 17, 2008
Received February 4, 2008

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Letter

Palladium-Catalyzed α-Arylation of Esters with Chloroarenes