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Synthesis of Sulfinamides


Recent Literature

Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions. Subsequent treatment with 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.

Eu(OTf)3 catalyzes a transsulfinamidation of primary sulfinamides with alkyl, aryl, and heterocyclic amines to provide diverse secondary and tertiary sulfinamides. Excellent catalytic activity and selectivity are achieved under mild reaction conditions.
D. Wen, Q. Zheng, C. Wang, T. Tu, Org. Lett., 2021, 23, 3718-3723.

Metal- and additive-free transsulfinamidations of N-unsubstituted sulfinamides and N-pivaloyl-protected sulfinamides with various amines provide both N-monosubstituted and N,N-disubstituted sulfinamides in good yields simply by heating. Preliminary experiments also indicate that alcohols can be used as nucleophiles too.
S. Tsuzuki, T. Kano, Org. Lett., 2023, 25, 6677-6681.

Reaction of methyl sulfinates with lithium amides followed oxidation of the resulting sulfinamides provides primary, secondary, and tertiary alkane-, arene- and heteroarenesulfonamides in high yields. This protocol avoids the use of hazardous, unstable, or volatile reagents and does not affect the configurational stability of the amines.
J. L. C. Ruano, A. Parra, F. Yuste, V. M. Mastranzo, Synthesis, 2008, 311-312.

The addition of an organometallic reagent to the commercially available DABSO as sulfur dioxide surrogate generates a metal sulfinate which is reacted with thionyl chloride. Trapping of the formed sulfinyl chloride intermediates in situ with a variety of nitrogen nucleophiles provides sulfinamides in good yields. The overall reaction is performed at room temperature in only 1.5 h.
P. K. T. Lo, G. A. Oliver, M. C. Willis, J. Org. Chem., 2020, 85, 5753-5760.