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Rhodium(III)-Catalyzed Cascade Cyclization/Electrophilic Amidation for the Synthesis of 3-Amidoindoles and 3-Amidofurans

Zhiyong Hu, Xiaofeng Tong* and Guixia Liu*

*East China University of Science and Technology, 130 Meilong Road, Shanghai 200237; Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: tongxfecust.edu.cn, guixiasioc.ac.cn

Z. Hu, X. Tong, G. Liu, Org. Lett., 2016, 18, 2058-2061.

DOI: 10.1021/acs.orglett.6b00689 (free Supporting Information)


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Abstract

A rhodium(III)-catalyzed cascade cyclization/electrophilic amidation using N-pivaloyloxylamides as the electrophilic nitrogen source provides 3-amidoindoles and 3-amidofurans under mild conditions with good functional group tolerance. The 3-amidoindoles can be converted to several heterocycle-fused indoles.

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proposed reaction mechanism



Key Words

indoles, benzofurans


ID: J54-Y2016