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

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Rhodium-Catalyzed C−H Functionalization of Indoles with Diazo Compounds: Synthesis of Structurally Diverse 2,3-Fused Indoles
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-10-20 01:50:56 , DOI: 10.1002/adsc.201700974
Mengying Gao _{1,

2} , Yaxi Yang ₂ , Hua Chen ₁ , Bing Zhou ₂

Affiliation

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.

中文翻译：

含重氮化合物的铑催化的吲哚CH-H功能化：结构上不同的2,3-熔融吲哚的合成

据报道，铑的重氮化合物对吲哚的C2-H官能化，然后向C = O或C = C键的分子内亲核加成，可合成2,3-稠合的吲哚。除受体/受体重氮化合物外，还广泛耐受了供体/受体重氮化合物，使各种2,3稠合的吲哚具有完美的非对映体控制能力。值得注意的是，通过简单地改变反应条件，在吲哚的C 2和C 7位置处的选择性CH 2-二烷基化反应也已经发展。这种对环境无害的转化在温和的条件下进行，并给出了唯一的副产物二氮。

更新日期：2017-10-20

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