Iron-catalyzed oxidation of tertiary amines: synthesis of β-1,3-dicarbonyl aldehydes by three-component C-C couplings

Weiping Liu; Jinhua Liu; Daisuke Ogawa; Yasushi Nishihara; Xingwei Guo; Zhiping Li

doi:10.1021/ol202749x

Iron-catalyzed oxidation of tertiary amines: synthesis of β-1,3-dicarbonyl aldehydes by three-component C-C couplings

Org Lett. 2011 Dec 2;13(23):6272-5. doi: 10.1021/ol202749x. Epub 2011 Nov 4.

Authors

Weiping Liu¹, Jinhua Liu, Daisuke Ogawa, Yasushi Nishihara, Xingwei Guo, Zhiping Li

Affiliation

¹ Department of Chemistry, Renmin University of China, Beijing 100872, China.

PMID: 22053949
DOI: 10.1021/ol202749x

Abstract

β-1,3-Dicarbonyl aldehydes were synthesized by iron-catalyzed oxidative reactions between 1,3-dicarbonyl compounds and two molecules of tertiary amines in the presence of tert-butyl hydroperoxide (TBHP). α,β-Unsaturated aldehydes generated by tertiary amine oxidation in situ act as key intermediates under mild reaction conditions.