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J Org Chem. 2002 Feb 22;67(4):1199-207.

Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams.

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  • 1Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France. baudoin@icsn.cnrs-gif.fr

Abstract

The palladium-catalyzed, two-step, one-pot borylation/Suzuki coupling (BSC) reaction was developed to synthesize sterically hindered 2,2'-disubstituted biphenyl and phenyl-indole compounds in a short, simple, and efficient manner from two easily accessible aryl halides. High yields can be obtained by choosing properly both components according to their rough electronic properties. The illustration of the utility of this method was provided by the solution and solid-phase synthesis of seven- or eight-membered biphenyl lactams 5a-e, as well as paullone 3a. These compounds exhibit moderate albeit significant cytotoxicities and may serve as structural models for future medicinal chemistry developments.

PMID:
11846663
[PubMed - indexed for MEDLINE]
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