title: Copper-Catalyzed Three-Component Reaction for Regioselective Aryl- and Heteroarylselenation of Indoles using Selenium Powder.
abstract: A new and efficient copper-catalyzed C3 aryl- and heteroarylselenation of indoles employing selenium powder has been developed. The advantages of this chemistry involve the use of cheap selenating reagents, tolerance of a variety of functional groups, and practicality. In addition, this protocol has been further elaborated in an intramolecular phenylselenation of a (hetero) aryl C-H bond to construct an important motif of benzoselenopheno[3,2-b]indole. A preliminary mechanism study suggests that the reaction starts with a Ullman-type selenation between aryl iodides and selenium, followed by an oxidative cross-coupling with indole. The utility of this method has been demonstrated in an efficient gram-scale synthesis and an application to the synthesis of tubulin polymerization inhibitor.
authors.affiliation: College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, People's Republic of China.
authors.forename: Dongping
authors.initials: D
authors.lastname: Luo
authors.affiliation: School of Pharmacy, Wenzhou Medical University , Wenzhou 325035, People's Republic of China.
authors.forename: Ge
authors.initials: G
authors.lastname: Wu
authors.affiliation: College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, People's Republic of China.
authors.forename: Hang
authors.initials: H
authors.lastname: Yang
authors.affiliation: College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, People's Republic of China.
authors.forename: Miaochang
authors.initials: M
authors.lastname: Liu
authors.affiliation: College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, People's Republic of China.
authors.forename: Wenxia
authors.initials: W
authors.lastname: Gao
authors.affiliation: College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, People's Republic of China.
authors.forename: Xiaobo
authors.initials: X
authors.lastname: Huang
authors.affiliation: College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, People's Republic of China.
authors.forename: Jiuxi
authors.initials: J
authors.lastname: Chen
authors.affiliation: College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, People's Republic of China.
authors.forename: Huayue
authors.initials: H
authors.lastname: Wu