Boron-Catalyzed Azide Insertion of α-Aryl α-Diazoesters

Htet Htet San, Chun-Ying Wang, Hai-Peng Zeng, Shi-Tao Fu, Min Jiang, Xiang-Ying Tang*

*School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, People’s Republic of China, Email: xytanghust.edu.cn

H. H. San, C.-Y. Wang, H.-P. Zeng, S.-T. Fu, M. Jiang, X.-Y. Tang, J. Org. Chem., 2019, 84, 4478-4485.

DOI: 10.1021/acs.joc.8b03278

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Abstract

A metal-free azide insertion of α-aryl α-diazoesters in the presence of B(C₆F₅)₃ as catalyst affords the corresponding products in good yields. The reaction offers easy operation, wide substrate scope, and mild conditions and tolerates alkene and alkyne functional groups without cyclopropanation or cyclopropenation side products. A one-pot synthesis of 1,2,3-triazoles is also described.

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Key Words

α-azidoesters, benzyl azides

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ID: J42-Y2019