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Deoxycyanamidation of Alcohols with N -Cyano- N -phenyl- p -methylbenzenesulfonamide (NCTS)

2017; American Chemical Society; Volume: 19; Issue: 14 Linguagem: Inglês

10.1021/acs.orglett.7b01710

1523-7060

James N. Ayres, Matthew W. Ashford, Yannick Stöckl, Vassili Prudhomme, Kenneth B. Ling, James A. Platts, Louis C. Morrill,

Catalytic C–H Functionalization Methods

The first one-pot deoxycyanamidation of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diverse range of tertiary cyanamides in excellent isolated yields. This approach exploits the underdeveloped desulfonylative (N–S bond cleavage) reactivity pathway of NCTS, which is more commonly employed for electrophilic C- and N-cyanation processes.