Issue 34, 2023

A facile one-pot synthesis of N-acyl-1-cyano-1,2,3,4-tetrahydroisoquinoline via a photoredox and Reissert-type reaction from 1,2,3,4-tetrahydroisoquinolines

Abstract

Herein we report a protocol for the direct α-cyanation/N-acylation of THIQs via a one-pot photoredox and Reissert-type reaction using air as the oxidant and acyl cyanide as the acyl and cyano source at ambient temperature. A set of various N-acyl-1-cyano THIQs were obtained in moderate to good yields. A plausible mechanism is suggested based on preliminary mechanistic studies.

Graphical abstract: A facile one-pot synthesis of N-acyl-1-cyano-1,2,3,4-tetrahydroisoquinoline via a photoredox and Reissert-type reaction from 1,2,3,4-tetrahydroisoquinolines

Supplementary files

Article information

Article type
Communication
Submitted
05 Jun 2023
Accepted
30 Jul 2023
First published
01 Aug 2023

New J. Chem., 2023,47, 15847-15851

A facile one-pot synthesis of N-acyl-1-cyano-1,2,3,4-tetrahydroisoquinoline via a photoredox and Reissert-type reaction from 1,2,3,4-tetrahydroisoquinolines

Z. Yuan, Z. Zhang, J. Liang, C. Lin, D. Peng, B. Cui, X. Mou, Y. Zhang and Y. Chen, New J. Chem., 2023, 47, 15847 DOI: 10.1039/D3NJ02600K

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