Issue 74, 2023

Electrochemical reductive cascade cyclization of o-alkynylated derivatives for saturated amides/amines

Abstract

An unprecedented reductive hydroamidative/hydroquinazolinative cascade cyclization of o-alkynylated derivatives was achieved via proton-coupled electron transfer (PCET) under electrolysis. In a single step, the rapid assembly of isoindolinones and novel isoindole-fused quinazolinones were achieved through electrolysis by the hydroamidation of amidyl/quinazolinone aminyl radicals with C–C triple bond addition via 5-exo-dig cyclization followed by olefinic reduction without external reductants. Control and cyclic voltammetry experiments support a mechanistic explanation of the electrochemical cascade, and these experiments indicate that the electrolyte is the source of hydrogen for the olefin reduction.

Graphical abstract: Electrochemical reductive cascade cyclization of o-alkynylated derivatives for saturated amides/amines

Supplementary files

Article information

Article type
Communication
Submitted
11 Jul 2023
Accepted
21 Aug 2023
First published
22 Aug 2023

Chem. Commun., 2023,59, 11125-11128

Electrochemical reductive cascade cyclization of o-alkynylated derivatives for saturated amides/amines

M. B. Reddy, S. Prabhu and R. Anandhan, Chem. Commun., 2023, 59, 11125 DOI: 10.1039/D3CC03350C

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