Synthesis of sulfinamides

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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.

Readily available and structurally diverse alkyl carboxylic acids can serve as the starting materials for sulfinamides, sulfonamides, and sulfonimidamides syntheses. The methods harness alkyl radical generation from carboxylic acids using acridine photocatalysts and 400 nm light with subsequent radical addition to sulfinylamine reagents, delivering sulfinamide products.
J. A. Andrews, J. Kalepu, C. F. Palmer, D. L. Poole, K. E. Christensen, M. C. Willis, J. Am. Chem. Soc., 2023, 145, 21623-21629.

The reaction of a N-silyl sulfinylamine reagent with Grignard, organolithium, or organozinc reagents provides a broad range of (hetero)aryl, alkenyl, and alkyl primary sulfinamides. Treatment of these primary sulfinamides with an amine in the presence of a hypervalent iodine reagent leads directly to sulfonimidamides.
M. Ding, Z.-X. Zhang, T. Q. Davies, M. C. Willis, Org. Lett., 2022, 24, 1711-1715.