American Chemical Society
ol6b01059_si_001.pdf (2.3 MB)

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

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journal contribution
posted on 2016-05-11, 00:00 authored by Tao Lei, Wen-Qiang Liu, Jian Li, Mao-Yong Huang, Bing Yang, Qing-Yuan Meng, Bin Chen, Chen-Ho Tung, Li-Zhu Wu
Irradiation of a mixture of enamines and α-bromo ketones, with a catalytic amount of Ir­(ppy)3 by visible light (λ = 450 nm), enables the production of various 2,5-diaryl-substituted pyrroles in good to excellent yields. The key intermediates in this reaction have been identified as 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 to undergo the Hantzsch reaction rapidly at ambient conditions.