Synthesis of Di- and Triarylmethanes through Palladium-Catalyzed Reductive Coupling of N-Tosylhydrazones and Aryl Bromides

Abstract

A palladium-catalyzed reductive coupling between N-tosylhydrazones and aryl bromides has been developed. The reaction provides an efficient method for the synthesis of diarylmethanes and triarylmethanes via the formation of C(sp²)–C(sp³) single bonds. This new methodology for the synthesis of diarylmethanes and triarylmethanes is featured by the ready availability of the starting materials, mild reaction conditions, and the tolerance of wide range of functional groups. The reaction follows a pathway including palladium carbene formation, migratory insertion, and reduction of the alkylpalladium(II) intermediate.

Key words

N-tosylhydrazone - cross-coupling - carbene - palladium - diarylmethane - triarylmethane

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