Copper-catalyzed decarboxylative Se insertion coupling of indoles and propiolic acids

A novel and efficient copper-catalyzed decarboxylative alkynylselenation of indoles with Se powder and propiolic acids has been developed. The outstanding advantages of this protocol not only nicely avoid the use of prefabricated arylselenation reagent and address the facile over-selention issues, but also enrich the chemistry of selenium powder. Importantly, this reaction could be extended to pyrrole, and the practical utility of this transformation has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid. The outstanding advantages of this protocol not only nicely avoid the use of prefabricated arylselenation reagent and address the facile over-selention issues, but also enrich the chemistry of selenium powder. Importantly, this reaction could be extended to pyrrole, and the practical utility of this transformation has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.