Atmospheric oxidative catalyst-free cross-dehydrogenative coupling of aldehydes with N-hydroxyimides. Issue 18 (3rd May 2017)

• Record Type: Journal Article
• Authors: Xu, Xiaohe; Li, Pingping; Huang, Yingyi; Tong, Chuo; Yan, YiYan; Xie, Yuanyuan
• Is Part Of: Tetrahedron letters. Volume 58:Issue 18(2017)
• Page Start: 1742
• Page End: 1746
• Publication Date: 2017-05-03
• Subjects: Catalyst-free -- Cross-dehydrogenative coupling -- Atmospheric oxidative -- Aldehydes -- N-Hydroxyimidates; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.03.064
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Catalyst-free protocol. Air as the terminal oxidant. Simple purification. Gram synthesis. One-pot synthesis amides. Abstract: Cross-dehydrogenative coupling (CDC) reactions of aldehydes with N -hydroxyimidates such as N -hydroxysuccinimide (NHSI), N -hydroxyphthalimide (NHPI) under catalyst-free conditions is described. Moreover, the desired products can be obtained simply by recrystallization from ethanol. This method is also applicable to the synthesis of amides in excellent yields. A radical mechanism of the type shown in Scheme 4 is proposed based upon the inhibition of the reaction in the presence of TEMPO.