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铱(III)催化苯甲酰乙腈的 C-H 活化与重氮化合物的串联环化反应构建取代苯并[de]色烯。

Rh(III)-Catalyzed C-H Activation of Benzoylacetonitriles and Tandem Cyclization with Diazo Compounds to Substituted Benzo[ de]chromenes.

机构信息

State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry , China Pharmaceutical University , 24 Tong Jia Xiang , Nanjing , Jiangsu 210009 , P. R. China.

State Key Laboratory of Drug Research and Key Laboratory of Receptor Research , Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road , Shanghai 201203 , China.

出版信息

Org Lett. 2018 Apr 6;20(7):1720-1724. doi: 10.1021/acs.orglett.8b00103. Epub 2018 Mar 22.

Abstract

Rh (III)-catalyzed C-H activation of benzoylacetonitriles in coupling with diazo compounds was developed to synthesize diversified substituted benzo[ de]chromenes via a formal (4 + 2) cycloaddition with a diazo compound and subsequent tandem (4 + 2) cycloaddition with another diazo compound. Intriguingly, synthesis of substituted benzo[ de]chromenes and their decarboxylation products could be realized by controlling the reaction conditions. These reactions have a broad range of substrates, moderate to good yields, and high regioselectivity.

摘要

铑(III)催化苯甲酰乙腈与重氮化合物的 C-H 活化反应,通过与重氮化合物的[4 + 2]环加成和与另一个重氮化合物的串联[4 + 2]环加成,合成了多种取代的苯并[de]色烯。有趣的是,通过控制反应条件,可以实现取代的苯并[de]色烯及其脱羧产物的合成。这些反应具有广泛的底物范围,中等至良好的产率和高区域选择性。

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