Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction

Chun-Huan Jiang; Xiantao Lei; Le Zhen; Hong-Jin Du; Xiaoan Wen; Qing-Long Xu; Hongbin Sun

doi:10.3762/bjoc.10.306

Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction

Beilstein J Org Chem. 2014 Dec 5:10:2892-6. doi: 10.3762/bjoc.10.306. eCollection 2014.

Authors

Chun-Huan Jiang¹, Xiantao Lei¹, Le Zhen¹, Hong-Jin Du¹, Xiaoan Wen¹, Qing-Long Xu¹, Hongbin Sun¹

Affiliation

¹ State Key Laboratory of Natural Medicines and Jiangsu Key Laboratory of Drug Discovery for Metabolic Disease, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China.

Abstract

Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolcular [1,5]-hydride shift/isomerization reaction has been realized, using the inherent reducing power of 3-pyrrolines. A series of N-arylpyrrole containing amines are obtained in high yields.

Keywords: C–H activation; Lewis acid; catalysis; hydride-shift; redox reaction.