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Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds
- Authors
- Kim, Seung Woo; Um, Tae-Woong; Shin, Seunghoon
- Issue Date
- Apr-2018
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.83, no.8, pp.4703 - 4711
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 83
- Number
- 8
- Start Page
- 4703
- End Page
- 4711
- ISSN
- 0022-3263
- Abstract
- Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Bronsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I-2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.
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Related Researcher
- Shin, Seung hoon
- COLLEGE OF NATURAL SCIENCES (DEPARTMENT OF CHEMISTRY)