title: Rhodium(III)- and iridium(III)-catalyzed C7 alkylation of indolines with diazo compounds.
abstract: A Rh(III)-catalyzed procedure for the C7-selective C-H alkylation of various indolines with α-diazo compounds at room temperature is reported. The advantages of this process are: 1) simple, mild, and pH-neutral reaction conditions, 2) broad substrate scope, 3) complete regioselectivity, 4) no need for an external oxidant, and 5) N2 as the sole byproduct. Furthermore, alkylation and bis-alkylation of carbazoles at the C1 and C8 positions have also been developed. More significantly, for the first time, a successful Ir(III)-catalyzed intermolecular insertion of arene C-H bonds into α-diazo compounds is reported.
authors.affiliation: Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203 (P. R. China), Fax: (+86) 21-50807288; Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
authors.forename: Wen
authors.initials: W
authors.lastname: Ai
authors.forename: Xueyan
authors.initials: X
authors.lastname: Yang
authors.forename: Yunxiang
authors.initials: Y
authors.lastname: Wu
authors.forename: Xuan
authors.initials: X
authors.lastname: Wang
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Li
authors.forename: Yaxi
authors.initials: Y
authors.lastname: Yang
authors.forename: Bing
authors.initials: B
authors.lastname: Zhou
mesh_terms: D000478:Alkylation; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D007211:Indoles; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D007211:Indoles; D007495:Iridium; C057812:indoline; D012238:Rhodium
keywords: CH activation; alkylation; indolines; iridium; rhodium