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

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

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

Author(s) -

James N. Ayres,

Matthew W. Ashford,

Yannick Stöckl,

Vassili Prudhomme,

Kenneth B. Ling,

James A. Platts,

Louis C. Morrill

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b01710

Subject(s) - cyanamide , chemistry , electrophile , reagent , sulfonyl , reactivity (psychology) , medicinal chemistry , bond cleavage , tertiary alcohols , alcohol , organic chemistry , catalysis , medicine , alkyl , alternative medicine , pathology

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.

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