Application of Fundamental Organometallic Chemistry to the Development of a Gold-Catalyzed Synthesis of Sulfinate Derivatives

Authors


  • This research was supported in part by a grant from the NIHGMS (RO1 GM073932). M.W.J. is grateful to the National Science Foundation (no. DGE1106400) and UC Berkeley for pre-doctoral research fellowships. N.P.M. acknowledges the National Institute of Health for a Kirchstein-NRSA postdoctoral fellowship. S.W.B. thanks Andrei Shavyna, Aaron Smith, and Kevin Hesp for helpful discussions. William J. Wolf (UC Berkeley) and Brian Samas (Pfizer) are thanked for assistance with X-ray crystallographic studies.

Abstract

The development of a gold(I)-catalyzed sulfination of aryl boronic acids is described. This transformation proceeds through an unprecedented mechanism which exploits the reactivity of gold(I)–heteroatom bonds to form sulfinate anions. Further in situ elaboration of the sulfinate intermediates leads to the corresponding sulfones and sulfonamides, two pharmacophores routinely encountered in drug discovery.

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