Categories: C-S Bond Formation >
Synthesis of allylic sulfides
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 efficient, indium triiodide-catalyzed substitution of the acetoxy group in alkyl, benzyl, allyl, and propargyl acetates with thiosilanes provides access to various thioethers.
Y. Nishimoto, A. Okita, M. Yasuda, A. Baba, Org. Lett., 2012, 14, 1846-1849.
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.
TAPC efficiently catalyzes the reaction of benzylic alcohols with aryl, heteroaryl, and alkyl thiols to afford thioethers in good to excellent yields. Furthermore, the reaction proceeds under metal-free and solvent-free conditions thus represents an interesting complement to known methods for thioether synthesis. A plausible mechanism is given.
K. Bahrami, M. M. Khodaei, N. Khodaboustan, Synlett, 2011, 2206-2210.