N-Alkylsulfonamides as Useful Carbon Electrophiles

The cleavage of the sp(3) carbon-nitrogen bonds in N-alkylsulfonamides has been utilized for the selective formation of various carbon-carbon and carbon-heteroatom bonds. When N-alkylsulfonamides undergo sp(3) carbon-nitrogen bond cleavage in the presence of acid catalysts, the resulting carbocations can react with a broad range of carbon, sulfur, nitrogen, oxygen, or hydride nucleophiles. On the other hand, basic conditions allow N-alkylsulfonamides to act as sp(3) carbon electrophiles in reactions with strong nucleophiles. In general, N-benzylic, N-allylic, and N-propargylic sulfonamides serve as suitable substrates, and their reactions with nucleophiles provide ready access to a wide range of functionalized molecules.