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

被引：41
|
作者：
Kim, Seung Woo
Um, Tae-Woong
Shin, Seunghoon [1 ]
机构：
[1] Hanyang Univ, Ctr New Direct Organ Synth CNOS, Dept Chem, 222 Wangsimni Ro, Seoul 04763, South Korea
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 08期
基金：
新加坡国家研究基金会;
关键词：
EFFICIENT CATALYST; BENZIL DERIVATIVES; AEROBIC OXIDATION; MOLECULAR-IODINE; ALPHA-DIKETONES; ALKYNES; AZIRIDINATION; CYCLIZATION; OLEFINS; ALKENES;
D O I：
10.1021/acs.joc.8b00484
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：4703 / 4711
页数：9
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