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

Autor:	Tae Woong Um, Seunghoon Shin, Seungwoo Kim
Rok vydání:	2018
Předmět:	010405 organic chemistry Organic Chemistry chemistry.chemical_element 010402 general chemistry Iodine 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Metal free Benzil Brønsted–Lowry acid–base theory
Zdroj:	The Journal of Organic Chemistry. 83:4703-4711
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.8b00484
Popis:	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 % I2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0ea84227760ee036daec6c6a60c87492 https://doi.org/10.1021/acs.joc.8b00484 Zobrazit plný text záznamu