Diaryliodoniums as Hybrid Hydrogen- and Halogen-Bond-Donating Organocatalysts for the Groebke-Blackburn-Bienaymé Reaction
Mikhail V. Il'in, Alexandra A. Sysoeva, Alexander S. Novikov and Dmitrii S. Bolotin*
*Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg 199034, Russian Federation,
Email: d.s.bolotin
spbu.ru
M. V. Il'in, A. A. Sysoeva, A. S. Novikov, D. S. Bolotin, J. Org. Chem., 2022, 87, 4569-4579.
DOI: 10.1021/acs.joc.1c02885
Abstract
Dibenziodolium triflate displays high catalytic activity for the Groebke-Blackburn-Bienaymé Reaction that leads to a series of imidazopyridines. This salt can play the role of a hybrid hydrogen- and halogen-bond-donating organocatalyst, which electrophilically activates the carbonyl and imine groups.
see article for more examples
Dibenziodolium triflate displays higher catalytic activity than diphenyliodonium triflate, as additional energy is required for the rotation of the phenyl ring during ligation of the substrate
Key Words
organocatalysis, multicomponent reactions, imidazo[1,2-a]pyridines
ID: J42-Y2022
