Issue 13, 2021

Electrooxidative tandem cyclization of N-propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives

Abstract

A series of N-propargylanilines (0.2 mmol) and sulfinic acids (0.5 mmol) afforded 3-arylsulfonylquinoline derivatives in high yields (70–93%) and low current efficiencies upon electrooxidation. Electrolyses were carried out in a one-compartment cell, under constant current and ambient conditions, in methanol-nBu4NBF4 containing pyridine (0.4 mmol), without any added chemical oxidant. A scale-up electrolysis carried out on 5 mmol of N-propargylaniline 1a gave 3-arylsulfonylquinoline 3aa in 65% yield and 56% current efficiency. A mechanistic hypothesis is presented.

Graphical abstract: Electrooxidative tandem cyclization of N-propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives

Supplementary files

Article information

Article type
Paper
Submitted
16 Jan 2021
Accepted
25 Mar 2021
First published
25 Mar 2021

Green Chem., 2021,23, 4733-4740

Electrooxidative tandem cyclization of N-propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives

J. Liu, M. Wang, L. Li and L. Wang, Green Chem., 2021, 23, 4733 DOI: 10.1039/D1GC00171J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements