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Rhodium(III)-Catalyzed Indole Synthesis Using N-N Bond as an Internal Oxidant

Baoqing Liu, Chao Song, Chao Sun, Shuguang Zhou and Jin Zhu*

*Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China, Email: jinznju.edu.cn

B. Liu, C. Song, C. Sun, S. Zhou, J. Zhu, J. Am. Chem. Soc., 2013, 135, 16625-16631.

DOI: 10.1021/ja408541c (free Supporting Information)



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Abstract

A Rh(III)-catalyzed cyclization of N-nitrosoanilines with alkynes enables a streamlined synthesis of indoles. The C-H activation-based intermolecular redox-neutral protocol uses an N-N bond as internal oxidant, which offers a valuable complement to the widely used N-O variants. The reaction tolerates various functional groups and can be conducted under acidic as well as basic conditions.

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Key Words

Indoles


ID: J48-Y2013