Palladium-Catalyzed Denitrogenative Cross-Coupling of Silicon-Masked, Aryl-Substituted Diazenes and Aryl Bromides

Abstract

A denitrogenative palladium-catalyzed C(sp²)–C(sp²) cross-coupling of aryl-substituted diazenes capped with a trimethylsilyl group and functionalized aryl bromides is reported. A PEPPSI™ catalyst in the presence of NaOt-Bu enables the activation of the N-aryl-N′-silyldiazene pronucleophile with concomitant loss of dinitrogen and subsequent coupling of the in-situ-formed aryl nucleophile. By this, biaryl compounds bearing a variety of substituents can be prepared.

Key words

biaryls - chemoselectivity - cross-coupling - denitrogenation - diazene - palladium - silicon

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