title: Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS).
abstract: BF(3)·OEt(2)-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.
authors.affiliation: Beijing National Laboratory of Molecular Sciences (BNLMS), College of Chemistry, Peking University, Beijing 100871, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jianbo
authors.initials: J
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry*; D014050:Toluene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000096926:Benzenesulfonamides
chemical_list: D007211:Indoles; D058116:Lewis Acids; D009570:Nitriles; D011758:Pyrroles; D013449:Sulfonamides; D014050:Toluene; C568587:N-cyano-N-phenyl-para-toluenesulfonamide; C025417:4-toluenesulfonamide; D000096926:Benzenesulfonamides