Synthesis of tetrahydroquinoline derivatives electrochemical hydrocyanomethylation or hydrogenation of quinolines with MeCN

A series of tetrahydroquinoline derivatives were selectively synthesized at room temperature via electrochemical hydrocyanomethylation of quinoline skeletons using acetonitrile as both a hydrogen source and a cyanomethyl precursor. When a bulky substituent was present at the C2 position, hydrogenati...

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2024-05, Vol.26 (9), p.516-5166
Main Authors: Xia, Jie, Wang, Dahan, Yang, Ruitong, Deng, Yujie, Deng, Guo-Jun
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of tetrahydroquinoline derivatives were selectively synthesized at room temperature via electrochemical hydrocyanomethylation of quinoline skeletons using acetonitrile as both a hydrogen source and a cyanomethyl precursor. When a bulky substituent was present at the C2 position, hydrogenation of quinoline derivatives dominated. Furthermore, a deuterium labeling experiment revealed that protons were derived from acetonitrile. This method features mild conditions, high efficiency, wide substrate scope, and good functional group tolerance. Electrochemical hydrocyanomethylation of quinoline skeletons employing acetonitrile as both a hydrogen resource and a cyanomethyl precursor has been described.
ISSN:1463-9262
1463-9270
DOI:10.1039/d4gc00164h