title: Rhodium-Catalyzed Cyanation of C(sp(2))-H Bond of Alkenes.
abstract: Efficient and selective rhodium-catalyzed cyanation of chelation-assisted C-H bonds of alkenes has been accomplished using environmentally benign N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as a cyanating reagent. The developed methodology tolerates various functional groups and allows the synthesis of diverse substituted acrylonitriles in good to excellent yields. Furthermore, the potential of the methodology was demonstrated through the formal synthesis of chlorpheniramine-based antagonist.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
authors.forename: Manthena
authors.initials: M
authors.lastname: Chaitanya
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
authors.forename: Pazhamalai
authors.initials: P
authors.lastname: Anbarasan
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002744:Chlorpheniramine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry; D014050:Toluene / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; C568587:N-cyano-N-phenyl-para-toluenesulfonamide; D009570:Nitriles; D013449:Sulfonamides; D014050:Toluene; D002744:Chlorpheniramine; D012238:Rhodium