文献类型：期刊文献

英文题名：Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles

作者：Zhang, Zhen[1];Tang, Xiangying[1];Xu, Qin[2,3];Shi, Min[1,2,3]

机构：[1]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China;[2]E China Univ Sci & Technol, Adv Mat Lab, Shanghai 200237, Peoples R China;[3]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2013

卷号：19

期号：32

起止页码：10625

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20133216582749);WOS:【SCI-EXPANDED(收录号:WOS:000322238800031)，CCR-EXPANDED(收录号:WOS:000322238800031)】；

基金：We thank the Shanghai Municipal Committee of Science and Technology (08dj1400100-2), the National Basic Research Program of China ((973)-2009CB825300), the Fundamental Research Funds for the Central Universities and the National Natural Science Foundation of China (21102166, 21072206, 20472096, 20872162, 20672127, 21121062, and 20732008) for financial support.

语种：英文

外文关键词：carbazoles; catalysis; cyclization; gold; indoles

摘要：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.