Zn-CuI-Mediated coupling of alkyl halides with vinyl sulfones, vinyl sulfonates and vinyl sulfonamides

ORGN 402

Matthew M. Zhao, matthew_zhao@merck.com, Chuanxing Qu, and Joseph E. Lynch. Process Research, Merck Research Laboratories, Merck & Co., Inc, P. O. Box 2000, Rahway, NJ 07065
A novel high yielding Zn/CuI mediated coupling method of alkyl halides with vinyl sulfones, vinyl sulfonates and vinyl sulfonamides is described. The reaction is applicable for primary, secondary and tertiary alkyl iodides and bromides. Alkyl chlorides, aryl and vinyl halides are unreactive under the reaction conditions. Formamide is found to be a critical solvent for the reaction.