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

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초록

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.

키워드

EFFICIENT CATALYST; BENZIL DERIVATIVES; AEROBIC OXIDATION; MOLECULAR-IODINE; ALPHA-DIKETONES; ALKYNES; AZIRIDINATION; CYCLIZATION; OLEFINS; ALKENES
제목
Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds
저자
Kim, Seung Woo; Um, Tae-Woong; Shin, Seunghoon
DOI
10.1021/acs.joc.8b00484
발행일
2018-04
유형
Article
저널명
The Journal of Organic Chemistry
권
83
호
8
페이지
4703 ~ 4711