Synthesis of allylic sulfides

Recent Literature

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.

Sn(OTf)₂ catalyzes a mild and efficient synthesis of allyl sulfides from allyl alcohols and thiols as substrates in dichloromethane at room temperature. A diverse range of allyl sulfides have been obtained with good to excellent yields after a reaction time of 12 hours.
Y. Chen, Z. Gao, Synthesis, 2022, 54, 5291-5299.

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.

Rh-catalyzed hydrothiolation of 1,3-dienes provides either secondary or tertiary allylic sulfides via selective addition of a thiol to the more substituted double bond. The catalyst tolerates a wide range of functional groups.
X.-H. Yang, R. T. Davison, V. M. Dong, J. Am. Chem. Soc., 2018, 140, 10443-10446.

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.

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.

Cyclopropenes undergo Rh-catalyzed hydrothiolation to provide cyclopropyl sulfides or allylic sulfides. The choice of bisphosphine ligand dictates whether the pathway involves ring-retention or ring-opening. Whereas the use of Josiphos ligands provides cyclopropyl sulfides in high enantio- and diastereoselectivities, DTBM-BINAP generates allylic sulfides with high enantio- and regiocontrol.
S. Nie, A. Lu, E. L. Kuker, V. M. Dong, J. Am. Chem. Soc., 2021, 143, 6176-6184.