title: Access to Six- and Seven-Membered 1,7-Fused Indolines via Rh(III)-Catalyzed Redox-Neutral C7-Selective C-H Functionalization of Indolines with Alkynes and Alkenes.
abstract: We report herein a new strategy for the Rh(III)-catalyzed redox-neutral C7-selective C-H activation/annulation of indolines to rapidly access various privileged 1,7-fused indolines by utilizing an oxidizing-directing group. For example, a Rh(III)-catalyzed redox-neutral C7-selective C-H functionalization of indolines with arylalkynes is described to directly access 7-membered 1,7-fused indolines. Moreover, an unprecedented intramolecular addition of an alkenyl-Cp*Rh(III) species to a carbamoyl moiety occurred to give 1H-pyrroloquinolinones when employing alkyl alkynes. Additionally, an efficient Rh(III)-catalyzed redox-neutral C7-selective C-H activation/alkenylation/aza-Michael addition of indolines is also developed to give 6-membered 1,7-fused indolines. The advantages of these processes are as follows: (1) mild and simple reaction conditions; (2) no need for an external oxidant; (3) broad scope of substrates; and (4) valuable six- or seven-membered 1,7-fused indolines as products.
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, P.R. China.
authors.forename: Xuan
authors.initials: X
authors.lastname: Wang
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, P.R. China.
authors.forename: Huanyu
authors.initials: H
authors.lastname: Tang
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, P.R. China.
authors.forename: Huijin
authors.initials: H
authors.lastname: Feng
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, P.R. China.
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Li
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, P.R. China.
authors.forename: Yaxi
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, P.R. China.
authors.forename: Bing
authors.initials: B
authors.lastname: Zhou
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000480:Alkynes; D007211:Indoles; D016877:Oxidants; C057812:indoline; D012238:Rhodium