Issue 14, 2015

Visible light mediated sp3 C–H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component reaction

Abstract

An efficient and high yield process for sp3 C–H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines is disclosed. This involves a visible light mediated photoredox Ugi-type reaction with carboxylic acids and isonitriles under aerobic conditions, employing Ru(bpy)3Cl2 as a photoredox catalyst and CH3CN as the solvent. CH3CN was found to be crucial for the process, and good to excellent yields were achieved for a wide variety of N-aryl-1,2,3,4-tetrahydroisoquinolines, carboxylic acids, and isonitriles. The developed methodology is attractive for the synthesis of a library of 1,2,3,4-tetrahydroisoquinolines.

Graphical abstract: Visible light mediated sp3 C–H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component reaction

Supplementary files

Article information

Article type
Paper
Submitted
01 Feb 2015
Accepted
26 Feb 2015
First published
26 Feb 2015

Org. Biomol. Chem., 2015,13, 4260-4265

Author version available

Visible light mediated sp3 C–H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component reaction

Y. Chen and G. Feng, Org. Biomol. Chem., 2015, 13, 4260 DOI: 10.1039/C5OB00201J

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