Metal-Free-Catalyzed Three-Component [2+2+2] Annulation Reaction of [60]Fullerene, Ketones, and Indoles: Access to Diverse [60]Fullerene-Fused 1,2-Tetrahydrocarbazoles

被引:14
作者
Ma, Jinliang [1 ]
Liu, Tong-Xin [1 ]
Zhang, Pengling [1 ]
Zhao, Xuna [1 ]
Zhang, Guisheng [1 ]
机构
[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Henan Key Lab Organ Funct Mol & Drug Innovat, Minist Educ,Sch Chem & Chem Engn,Key Lab Green Ch, Xinxiang 453007, Henan, Peoples R China
关键词
ONE-POT; FULLERENE DERIVATIVES; MOLECULAR-IODINE; DIRECT ARYLATION; CHEMISTRY; EFFICIENT; CYCLOADDITION; BIOLOGY; WATER; C-60;
D O I
10.1021/acs.orglett.1c00195
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of metal-free-catalyzed multicomponent annulation reaction of [60]fullerene has been developed for concise and efficient construction of novel [60]fullerene-fused 1,2-tetrahydrocarbazoles. Using inexpensive and readily available I-2 as a catalyst, [60]fullerene, ketones, and indoles undergo a formal [2+2+2] annulation process to conveniently assemble diverse 1,2-tetrahydrocarbazoles. Mechanistic studies indicate that this reaction proceeds through I-2-promoted generation of a 3-vinylindole structure with the characteristics of a conjugated diene followed by cycloaddition to [60]fullerene.
引用
收藏
页码:1775 / 1781
页数:7
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