title: Substituent electronic effects govern direct intramolecular C-N cyclization of N-(Biphenyl)pyridin-2-amines induced by hypervalent iodine(III) reagents.
abstract: The hypervalent iodine(III) reagent-induced the direct intramolecular C-N cyclization of N-(biphenyl)pyridin-2-amines to 6-arylbenzimidazoles and N-pyridinyl-9H-carbazoles is presented. The substituent electronic effects governing the formation of benzimidazoles and carbazoles from the reaction of N-(biphenyl)pyridin-2-amines with hypervalent iodine(III) reagents is investigated. Radical trapping and UV-vis spectroscopic experiments on the detection of the cation radical are carried out. Rational mechanisms for these reactions are presented. The selective intramolecular C-N and C-O cyclization of N-(biphenyl)acetamides based on the substituent electronic effects is also presented.
authors.affiliation: Department of Chemistry, National Sun Yat-sen University , Kaohsiung, Taiwan 804.
authors.forename: Jean-Ho
authors.initials: JH
authors.lastname: Chu
authors.forename: Wen-Ting
authors.initials: WT
authors.lastname: Hsu
authors.forename: Yi-Hua
authors.initials: YH
authors.lastname: Wu
authors.forename: Meng-Fan
authors.initials: MF
authors.lastname: Chiang
authors.forename: Nan-Hai
authors.initials: NH
authors.lastname: Hsu
authors.forename: Hao-Ping
authors.initials: HP
authors.lastname: Huang
authors.forename: Ming-Jung
authors.initials: MJ
authors.lastname: Wu