Organic letters

Palladium-catalyzed synthesis of diarylmethanes: Exploitation of carbanionic leaving groups

JR Schmink, NE Leadbeater

Index: Schmink, Jason R.; Leadbeater, Nicholas E. Organic Letters, 2009 , vol. 11, # 12 p. 2575 - 2578

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Citation Number: 33

Abstract

A novel route to the synthesis of diarylmethanes via a Pd-catalyzed α-arylation of benzyl ketones is reported. By harnessing the inherent reactivity of enolates, it is possible to circumvent the need for a transmetalating reagent such as boron for the coupling. Additionally, the two phenyl rings of the intermediate are exploited to stabilize the high- energy carbanionic leaving group in a straightforward synthesis.