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Synthesis of allylic sulfides

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A nickel(0) triethyl phosphite complex promotes the reaction of allylic acetates with thiols to produce allylic sulfides with retention of configuration without allylic rearrangement. A similar reaction of allylic acetates with alcohols and phenols also proceeds with retention of regio- and stereochemistry.
Y. Yatusmonji, Y. Ishida, A. Tsubouchi, T. Takeda, Org. Lett., 2007, 9, 4603-4606.


An iridium-catalyzed regio- and enatioselective allylation of allyl carbonates with aliphatic thiols as the nucleophile in dichloromethane enables the regioselective synthesis of branched allyl sulfides in good yields and high enantioselectivity.
N. Gao, S. Zheng, W. Yang, X. Zhao, Org. Lett., 2011, 13, 1514-1516.