Organic Letters
Organic Letters
4 years ago

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

Deoxycyanamidation of Alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)
Matthew W. Ashford, James A. Platts, Kenneth B. Ling, Yannick Stöckl, Vassili Prudhomme, James N. Ayres, Louis C. Morrill
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01710

DOI: 10.1021/acs.orglett.7b01710

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