title: Gold-catalyzed cyclization of 1-(indol-3-yl)-3-alkyn-1-ols: facile synthesis of diversified carbazoles.
abstract: Efficient cyclization of 1-(indol-3-yl)-3-alkyn-1-ols in the presence of a cationic gold(I) complex, leading to annulated or specific substituted carbazoles, was observed. Depending on the reaction conditions and substitution pattern, divergent reaction pathways were discovered, furnishing diversified carbazole structures. Cycloalkyl-annulated [b]carbazoles are obtained through 1,2-alkyl migration of the metal-carbene intermediates; cycloalkyl-annulated [a]carbazoles are formed through a Wagner-Meerwein-type 1,2-alkyl shift; carbazole ethers are constructed through ring-opening of the cyclopropyl group by nucleophilic attack of water or an alcohol.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, P.R.China.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Zhang
authors.forename: Xiangying
authors.initials: X
authors.lastname: Tang
authors.forename: Qin
authors.initials: Q
authors.lastname: Xu
authors.forename: Min
authors.initials: M
authors.lastname: Shi
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D000480:Alkynes; D002227:Carbazoles; D007211:Indoles; D012997:Solvents; C041514:carbazole; D006046:Gold
keywords: carbazoles; catalysis; cyclization; gold; indoles