Photoinduced oxidative cyclization of dithienylarenes

Zsignár-Nagy, Barnabás and Kümmel, Viktória and Gazdag, Tamás and Mayer, Péter József and Bokor, Zsófia and Holczbauer, Tamás and London, Gábor (2025) Photoinduced oxidative cyclization of dithienylarenes. Tetrahedron Green Chem, 5. No.-100076.

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Abstract

A photoinduced electrocyclization followed by aerobic oxidation of 1,2-dithienylarene derivatives is described as a greener alternative to direct aryl-aryl couplings. The formation of the naphthodithiophene type products was monitored by UV–vis spectroscopy. Naphthodithiophenes with different structural features and electronic characters were accessed. Oxidative cyclization using the combination of BF 3 ⋅Et 2 O and DDQ was a complementary approach to confirm the formation of the desired products. The method was also applicable to 2,3- dithienylbiphenylene having a backbone with antiaromatic character.

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