title: Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.
abstract: Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2resulted in the formation of indole aminal products.
authors.affiliation: Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.
authors.forename: Gerardo X
authors.initials: GX
authors.lastname: Ortiz
authors.affiliation: Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.
authors.forename: Brett N
authors.initials: BN
authors.lastname: Hemric
authors.affiliation: Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.
authors.forename: Qiu
authors.identifier: 0000-0002-6803-9556
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001557:Benzenesulfonates / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry
chemical_list: D000577:Amides; D000588:Amines; D001557:Benzenesulfonates; D002712:Chlorides; D007211:Indoles; D017967:Zinc Compounds; C016837:zinc chloride