Categories: N-S Bond Formation >
Synthesis of Sulfinamides
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.
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.