Zn/CuI-mediated coupling of alkyl halides with vinyl sulfones, vinyl sulfonates, and vinyl sulfonamides.
A novel high-yielding Zn/CuI-mediated coupling method of alkyl halides with vinyl sulfones, vinyl sulfonates, and vinyl sulfonamides is described. This protocol is applicable for primary, secondary, and tertiary alkyl iodides and bromides. Alkyl chlorides and aryl and vinyl halides were unreactive under the reaction conditions. Formamide was found to be a superior solvent for obtaining high yields.
Zhao
Matthew M
MM
Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, NJ 07065, USA. matthew_zhao@merck.com
Qu
Chuanxing
C
Lynch
Joseph E
JE
D003300:Copper / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013449:Sulfonamides / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D006219:Halogens; D013449:Sulfonamides; D013450:Sulfones; D013451:Sulfonic Acids; C009873:divinyl sulfone; D003300:Copper; D015032:Zinc