Organic Chemistry Portal



Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds

Seung Woo Kim, Tae-Woong Um and Seunghoon Shin*

*Department of Chemistry, Center for New Directions in Organic Synthesis (CNOS) and Research Institute for Natural Sciences, Hanyang University, 222-Wangsimni-ro, Seongdong-gu, Seoul 04763, Korea, Email:

S. W. Kim, T.-W. Um, S. Shin, J. Org. Chem., 2018, 83, 4703-4711.

DOI: 10.1021/acs.joc.8b00484 (free Supporting Information)

see article for more reactions


The use of pyridine-N-oxides as oxidants under molecular iodine catalysis enables a rapid, metal-free dioxygenation of ynamides. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to provide various benzil derivatives.

see article for more examples

Key Words

α-keto amides, N-oxides

ID: J42-Y2018