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

Morten Jørgensen, Sunwoo Lee, Xiaoxiang Liu, Joanna P. Wolkowski and John F. Hartwig*

*Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, Email: john.hartwigyale.edu

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

DOI: 10.1021/ja027643u (free Supporting Information)

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Abstract

A palladium-catalyzed coupling of aryl halides and ester enolates produced α-aryl esters in high yields at room temperature. The reaction was highly tolerant of functionalities and substitution patterns on the aryl halide. Improved protocols for the selective monoarylation of tert-butyl acetate and the efficient arylation of α,α-disubstituted esters were developed with LiNCy₂ as base and P(t-Bu)₃ as ligand.

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Key Words

substituted esters, α-arylation

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ID: J48-Y2002-1310