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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:

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


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.

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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