Issue 6, 2016

Dual C–H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels–Alder reaction

Abstract

Described herein is the first example of the application of an iminium intermediate generated by visible-light photocatalyzed oxidation in an inverse electron-demand aza-Diels–Alder reaction. This dual functionalization of both C(sp3)–H and C(sp2)–H bonds of N-aryl tetrahydroisoquinolines represents a valuable example for access to polycycles with high diastereoselectivity.

Graphical abstract: Dual C–H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels–Alder reaction

Supplementary files

Article information

Article type
Communication
Submitted
26 Oct 2015
Accepted
12 Nov 2015
First published
13 Nov 2015

Chem. Commun., 2016,52, 1190-1193

Author version available

Dual C–H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels–Alder reaction

G. Xu, C. Li, M. Liu, J. Cao, Y. Luo and P. Xu, Chem. Commun., 2016, 52, 1190 DOI: 10.1039/C5CC08833J

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