Photoinduced regioselective arylation of N-vinyllactams and methylthiazoles by tetrachlorophthalimides
•Regioselective arylation of N-vinyllactams and methylthiazoles•Z-isomer is the main product of the photoreaction of N-vinyllactams and tetrachlorophthalimides•Reaction mechanism for the metal-free coupling reactions is discussed.
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
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 271, 1 November 2013, Pages 85–92