Iron-Catalyzed Trifluoromethylation of Indole-Tethered Alkene Enables Synthesis of CF3-Containing Spiroindolenines and Tetrahydrocarbazoles

被引：2

作者：

Zhao, Yilin ^{[1
]}

Hou, Tingting ^{[1
]}

Zhang, Liming ^{[1
]}

Wang, Xue ^{[1
]}

Hou, Jingli ^{[1
]}

Liu, Yangping ^{[1
]}

Han, Guifang ^{[1
]}

Song, Yuguang ^{[1
]}

机构：

[1] Tianjin Med Univ, Sch Pharm, Tianjin Key Lab Technol Enabling Dev Clin Therapeu, 22 Qixiangtai Rd, Tianjin 300070, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 18期

关键词：

dearomatization; iron; radical reaction; spirocarbocycle; trifluoromethylation; ASYMMETRIC ALLYLIC DEAROMATIZATION; ENANTIOSELECTIVE SYNTHESIS; FACILE SYNTHESIS; N-HETEROCYCLES; BOND FORMATION; FLUORINE; REAGENTS; FUNCTIONALIZATION; ACCESS;

D O I：

10.1002/ejoc.202300253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iron-catalyzed trifluoromethylation of indole-tethered alkene with Togni's reagent to construct CF3-containing spiro[indole-3,3 '-pyrrolidine] and tetrahydrocarbazole derivatives under mild and convenient conditions has been disclosed. Mechanistic studies indicate that the reaction proceed through a CF3 radical addition to the alkene, followed by sequential dearomatizing spiocyclization of the indole and oxidation to afford the spiro[indole-3,3 '-pyrrolidine] derivatives. Meanwhile, when the substituent at the C2 position of the indole is hydrogen, the CF3-containing tetrahydrocarbazole is obtained through trifluoromethylation of alkene and cyclization of indole.

引用

页数：5

共 23 条

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[23] Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel-Crafts reaction
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