Categories: C-S Bond Formation >
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.
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.
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.
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.