Rhodium-Catalyzed C-H Functionalization of Indoles with Diazo Compounds: Synthesis of Structurally Diverse 2,3-Fused Indoles

被引：23

作者：

Gao, Mengying ^{[1
,2
]}

Yang, Yaxi ^{[2
]}

Chen, Hua ^{[1
]}

Zhou, Bing ^{[2
]}

机构：

[1] Hebei Univ, Coll Chem & Environm Sci, Key Lab Chem Biol Hebei Prov, Baoding 071002, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, Dept Med Chem, 555 Zu Chong, Shanghai 201203, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 01期

关键词：

Cp*Rh(III) catalyst; C-H activation; Diazo compounds; 2,3-fused indoles; NONREARRANGED MONOTERPENOID UNIT; ALPHA-DIAZOCARBONYL COMPOUNDS; N-TOSYLHYDRAZONES; BOND ACTIVATION; CARBENOID FUNCTIONALIZATION; RH(III)-CATALYZED SYNTHESIS; CASCADE REACTIONS; COMPOUNDS ACCESS; FUSED INDOLES; ALKYNES;

D O I：

10.1002/adsc.201700974

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A Rhodium-catalyzed C2-H functionalization of indoles with diazo compounds, followed by intramolecular nucleophilic addition to C=O or C=C bonds, is reported for divergent synthesis of 2,3-fused indoles. Besides acceptor/acceptor diazo compounds, donor/acceptor diazo compounds are broadly tolerated, giving various 2,3-fused indoles with perfect diastereocontrol. Notably, a selective C-H dialkylation reaction at C2 and C7 position of indoles has also been developed by simply changing the reaction conditions. This environmentally benign transformation proceeds under mild conditions and gives dinitrogen as the only by-product.

引用

页码：100 / 105

页数：6

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