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Palladium-Catalyzed α-Arylation of Esters with Chloroarenes

Takuo Hama and John F. Hartwig*

*Department of Chemistry, University of Illinois Urbana-Champaign, Box 58-6, Urbana, Illinois 61801, Email: jhartwiguiuc.edu

T. Hama, J. F. Hartwig, Org. Lett., 2008, 10, 1549-1552.

DOI: 10.1021/ol800258u (free Supporting Information)


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Abstract

Palladium-catalyzed α-arylations of chloroarenes with the sodium enolates of tert-butyl propionate and methyl isobutyrate occur in high yields using P(t-Bu)3 as ligand. 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.

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Efficient Synthesis of α-Aryl Esters by Room-Temperature Palladium-Catalyzed Coupling of Aryl Halides with Ester Enolates

M. Jørgensen, S. Lee, X. Liu, J. P. Wolkowski, J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 12557-12565.


Key Words

α-Arylation


ID: J54-Y2008-1050