Organic Chemistry Portal

Abstracts

Search:

FeCl3 as an Ion-Pairing Lewis Acid Catalyst. Formation of Highly Lewis Acidic FeCl2+ and Thermodynamically Stable FeCl4- To Catalyze the Aza-Diels-Alder Reaction with High Turnover Frequency

Rei Tomifuji, Kazuki Maeda, Toshifumi Takahashi, Takuya Kurahashi*, Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Email: kurahashi.takuya.2ckyoto-u.ac.jp, matsubara.seijiro.2ekyoto-u.ac.jp

R. Tomifuji, J. Maeda, T. Takahashi, T. Kurahashi, S. Matsubara, Org. Lett., 2018, 20, 7474-7477.

DOI: 10.1021/acs.orglett.8b03249 (free Supporting Information)


see article for more reactions

Abstract

The ion-paired Lewis acid [FeCl2]+[FeCl4]- generated by the in situ disproportionation of FeCl3 catalyzes an aza-Diels-Alder reaction of nonactivated dienes and imines.

see article for more examples



Key Words

Diels-Alder reaction, N-heterocycles


ID: J54-Y2018