Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst.

Chem Commun (Camb) 2017 Mar;53(26):3689-3692

College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei 430072, People's Republic of China. and State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China.

In this work, a direct C-H activation of thiophenes was presented via an oxidation pathway under visible-light irradiation, in which the thiophene radical cation serves as the key intermediate. Various thiophenes and azoles could be transformed into the corresponding amination products well, and HO was the only byproduct which is environmentally benign. Our results showed that tert-butyl nitrite (TBN) served as the electron transfer mediator and O as the terminal oxidant to regenerate the photocatalyst DDQ and revive the photocatalytic cycle.

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http://dx.doi.org/10.1039/c7cc01339fDOI Listing
March 2017
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