Copper-catalyzed functionalization/transformation of styrenes with polyhaloalkanes and arenes enables the synthesis of heteroarene-containing gem-dihaloalkenes

A new copper-catalyzed three-component functionalization/transformation of styrenes using polyhaloalkanes and arenes is disclosed. The polyhaloalkanes generate the corresponding poylalkyl radicals which are then utilized in the copper-catalyzed alkene functionalization enabling the construction of gem-dichloro-, gem-dibromo-, and monobromo-alkene and acrylonitrile derivatives. Various indoles and styrenes featuring a wide range of substrates and functional groups are tolerated by the reaction, thus allowing the synthesis of versatile functionalized heteroarene-containing gem-dihaloalkenes, which are important structural backbones in bioactive molecules.

Automated summary

A new copper-catalyzed three-component functionalization/transformation of styrenes using polyhaloalkanes and arenes is discovered. The polyhaloalkanes generate corresponding poylalkyl radicals which are then utilized in the copper-catalyzed alkene functionalization, leading to the construction of various alkene derivatives. This method tolerates a wide range of substrates and functional groups, enabling the synthesis of versatile heteroarene-containing gem-dihaloalkenes, which are important backbones in bioactive molecules.