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Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones

Junwon Choi, Pablo Martín-Gago and Gregory C. Fu*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: gcfucaltech.edu

J. Choi, P. Martín-Gago, G. C. Fu, J. Am. Chem. Soc., 2014, 136, 12161-12165.

DOI: 10.1021/ja506885s


Abstract

Ni-catalyzed stereoconvergent Negishi arylations and alkenylations of racemic α-bromosulfonamides and -sulfones furnish cross-coupling product in very good ee and yield for an array of reaction partners. Mechanistic studies are consistent with the generation of a radical intermediate.

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Key Words

sulfones, benzylsulfones, sulfonamides, Negishi coupling


ID: J48-Y2014