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通过铑(III)催化的芳基硝酮的 C-H 活化与重氮化合物偶联合成 2,3-二取代 NH 吲哚。

Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds.

机构信息

State Key Laboratory of Applied Organic Chemistry, Lanzhou University Gansu and Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province , Lanzhou 730000, People's Republic of China.

Zhongwei High-Tech Institute of Lanzhou University , Zhongwei, Ningxia 755500, China.

出版信息

J Org Chem. 2017 Nov 3;82(21):11505-11511. doi: 10.1021/acs.joc.7b02105. Epub 2017 Oct 2.

DOI:10.1021/acs.joc.7b02105
PMID:28922912
Abstract

A rhodium-catalyzed intermolecular coupling between arylnitrones and diazo compounds by C-H activation/[4 + 1] annulation with a C(N)-C(acyl) bond cleavage is reported, and 2,3-disubstituted NH indoles are directly synthesized in up to a 94% yield. A variety of functional groups are applicable to this reaction to give the corresponding products with high selectivity. Compared to other previously reported Rh(III)-catalyzed synthesis of homologous series, this method is simpler, more general, and more efficient.

摘要

报道了铑催化的芳基硝酮与重氮化合物通过 C-H 活化/[4+1]环加成反应的分子间偶联反应,其中 C(N)-C(酰基)键断裂,直接合成了 2,3-二取代的 NH 吲哚,产率高达 94%。该反应可适用于多种官能团,以高选择性得到相应产物。与其他先前报道的 Rh(III)催化的同系物合成方法相比,该方法更简单、更通用、更高效。

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