Dissymmetrization of benzothiadiazole by direct C–H arylation: A way to symmetrical and unsymmetrical elongated π-conjugated molecules
Résumé
5-(7-Bromo-2,1,3-benzothiadiazol-4-yl)-2-thiophenecarbaldehyde is a small building block of great interest for its use in the elaboration of symmetrical or unsymmetrical donor–acceptor π-conjugated molecules for optoelectronic applications. Herein, a convenient, one-pot, two-component synthesis of this intermediate is reported, based upon a palladium-catalysed, phosphine- and additive-free, direct C–H arylation process. The synthesis has been studied in depth to obtain optimum yields and selectivity by an efficient and environmentally friendly strategy for sustainable synthesis.