Categories: S-O Bond Formation >
Synthesis of sulfinates and sulfinic acids
Alkyl arenesulfinates and S-thiosulfinates are readily prepared in good yields by the reaction of sulfinic acids and alcohols or thiols, respectively, in the presence of lanthanide(III) triflates as catalysts.
J. Drabowicz, M. Kwiatkowska, P. Kiełbasiński, Synthesis, 2008, 3563-3546.
A simple and efficient method for converting methyl sulfones to sulfinic acids involves alkylation with a benzylic halide, followed by in situ elimination of the resulting styrene in the presence of excess base to yield a sulfinic acid in a single reaction process.
D. R. Gauthier, Jr., N. Yoshikawa, Org. Lett., 2016, 18, 5994-5997.
Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions. Subsequent treatment with a various nitrogen, carbon, or oxygen nucleophiles affords a wide range of sulfinic acid amides, new sulfoxides, and sulfinic acid esters.
J. Wei, Z. Sun, Org. Lett., 2015, 17, 5396-5399.
A mild, late-stage conversion of primary sulfonamides to several other other functional groups occurs via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed N-sulfonylimines. This method tolerates common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds.
P. S. Fier, K. M. Maloney, J. Am. Chem. Soc., 2019, 141, 1441-1445.
Sulfinyl transfer agents based on cinchona alkaloids quinine and quinidine as chiral auxiliaries have been developed.
B. Z. Lu, F. Jin, Y. Zhang, X. Wu, S. A. Wald, C. H. Senanayake, Org. Lett., 2005, 7, 1465-1468.
An oxidation-free method provides sulfinic acids and sulfinate salts from easily prepared sulfone-substituted benzothiazole derivatives under mild reaction conditions. One-pot syntheses of sulfones and sulfonamides are also described.
J. J. Day, D. L. Neill, S. Xu, M. Xian, Org. Lett., 2017, 19, 3819-3822.