2-Halogenoimidazolium salt catalyzed aza-Diels-Alder reaction through halogen-bond formation

Youhei Takeda; Daichi Hisakuni; Chun-Hsuan Lin; Satoshi Minakata

doi:10.1021/ol503426f

2-Halogenoimidazolium salt catalyzed aza-Diels-Alder reaction through halogen-bond formation

Org Lett. 2015 Jan 16;17(2):318-21. doi: 10.1021/ol503426f. Epub 2014 Dec 31.

Authors

Youhei Takeda¹, Daichi Hisakuni, Chun-Hsuan Lin, Satoshi Minakata

Affiliation

¹ Frontier Research Base for Global Young Researchers, Graduate School of Engineering and ‡Department of Applied Chemistry, Graduate School of Engineering, Osaka University , Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.

PMID: 25551775
DOI: 10.1021/ol503426f

Abstract

2-Halogenoimidazolium salts are found to catalyze aza-Diels-Alder reaction of aldimines with Danishefsky diene in an efficient manner. Comparative studies and titration experiments support the formation of halogen bonding between imines and catalysts.