Gold‐Catalyzed Cyclization of 1‐(Indol‐3‐yl)‐3‐alkyn‐1‐ols: Facile Synthesis of Diversified Carbazoles |
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| Authors: | Zhen Zhang Dr. Xiangying Tang Dr. Qin Xu Prof. Dr. Min Shi |
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| Affiliation: | 1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032 (P.R.China), Fax: (+86)?21‐64166128;2. Laboratory for Advanced Materials & Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237 (P.R.China) |
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| 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. |
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| Keywords: | carbazoles catalysis cyclization gold indoles |
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