Categories: C-S Bond Formation >
Synthesis of sulfonyl chlorides
A clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is simple, environment- and worker-friendly. The procedure uses readily accessible reagents, offers safe operations and easy purification without chromatography, and affords high yields.
Z. Yang, B. Zhou, J. Xu, Synthesis, 2014, 46, 225-229.
A simple NaClO2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts enables a convenient, safe, and environmentally benign synthesis of diverse sulfonyl chlorides in high yields. The procedure is also applicable to other substrates such as thiols, disulfides, thioacetates, and xanthates.
Z. Yang, Y. Zheng, J. Xu, Synlett, 2013, 24, 2165-2169.
Structurally diverse sulfonyl chlorides were synthesized via N-chlorosuccinimide chlorosulfonation in good yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea. In large-scale syntheses, the water-soluble byproduct succinimide can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite.
Z. Yang, J. Xu, Synthesis, 2013, 45, 1675-1682.
The bench-stable colorless solid charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, can replace gaseous sulfur dioxide in organic synthesis. Reactions with Grignard reagents form sulfinates, which can then be converted in situ to sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides.
H. Woolven, C. Gonzáles-Rodríguez, I. Marco, A. L. Thompson, M. C. Willis, Org. Lett., 2011, 13, 4876-4878.