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Visible Light Initiated Hantzsch Synthesis of 2,5-Diaryl-Substituted Pyrroles at Ambient Conditions

Tao Lei, Wen-Qiang Liu, Jian Li, Mao-Yong Huang, Bing Yang, Qing-Yuan Meng, Bin Chen, Chen-Ho Tung and Li-Zhu Wu*

*Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190, P. R. China, Email: lzwumail.ipc.ac.cn

T. Lei, W.-Q. Liu, J. Li, M.-Y. Huang, B. Yang, Q.-Y. Meng, B. Chen, C.-H. Tung, L.-Z. Wu, Org. Lett., 2016, 18, 2479-2482.

DOI: 10.1021/acs.orglett.6b01059 (free Supporting Information)


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Abstract

The visible-light-mediated reaction of enamines with α-bromo ketones, with a catalytic amount of Ir(ppy)3, enables the production of various 2,5-diaryl-substituted pyrroles in very good yields. The key intermediates in this reaction are alkyl radicals, generated from single-electron transfer from the photoexcited Ir(ppy)3* to α-bromo ketones, which subsequently react with a broad range of enamines.

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Key Words

pyrroles


ID: J54-Y2016