Photoinduced regioselective arylation of N-vinyllactams and methylthiazoles by tetrachlorophthalimides

Photoinduced reactions of 4,5,6,7-tetrahalophthalimides (1a–1h) with selected N-vinyllactams (N-vinylpyrrolidinone, N-vinylcaprolactam) and methylthiazoles respectively lead to dehydrohalogenative coupling reactions between the phthalimide and these heterocycles. These mild and metal-free coupling reactions result in regioselective and stereoselective arylation of the heterocycles by the phthalimide, with the Z-isomer as the main products. Reaction mechanism for the photo-reactions is discussed