Palladium-Catalyzed Direct Arylation of Methyl Sulfoxides with Aryl Halides

T Jia, A Bellomo, KEL Baina, SD Dreher…

Index: Jia, Tiezheng; Bellomo, Ana; Baina, Kawtar El; Dreher, Spencer D.; Walsh, Patrick J. Journal of the American Chemical Society, 2013 , vol. 135, # 10 p. 3740 - 3743

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Citation Number: 58

Abstract

The palladium-catalyzed α-arylation of unactivated sulfoxides has been developed. The weakly acidic α-protons of sulfoxides are reversibly deprotonated by LiO t Bu, and a palladium phosphine complex facilitates the arylation. A variety of aryl methyl sulfoxides were coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under ...