Co-Catalyzed Reductive Cross-Couplings of Csp(3)-S with C-allyl-O Electrophiles to form Csp(3)-Csp(3) Bonds

Cross-electrophilic coupling of various benzyl sulfonium salts with Callyl-O electrophiles is described using a simple Co-Mn catalytic system. This catalytic system is able to activate both the stable Csp(3)-S bond of sulfonium salts and the Csp(3)-O bond of allylic acetate or ether under mild reaction conditions to form various functionalized alkyl olefinic compounds. Allyl methyl ethers were employed for the first time in transition metal-catalyzed cross-electrophilic coupling to build Csp(3)-Csp(3 )bonds. Preliminary mechanistic studies suggested the involvement of benzyl radicals generated from C-S bond cleavage through a single electron transfer.