On the Route to the Photogeneration of Heteroaryl Cations. The Case of Halothiophenes

…, F Chiesa, S Protti, A Albini, M Fagnoni

Index: Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo Organic and Biomolecular Chemistry, 2005 , vol. 3, # 15 p. 2868 - 2871

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Abstract

2-Chloro-, 2-bromo-, and 2-iodothiophenes undergo photochemical dehalogenation via the triplet state. In the presence of suitable π-bond nucleophiles, thienylation occurs with modest yield from chloro and bromo derivatives (via photogenerated triplet 2-thienyl cation). Specific trapping by using oxygen along with computational analysis carried out by means of a density functional method support that, in the case of iodo derivatives, homolytic thienyl–I ...