Issue 19, 2022

A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation

Abstract

An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate.

Graphical abstract: A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation

Supplementary files

Article information

Article type
Edge Article
Submitted
07 3月 2022
Accepted
09 4月 2022
First published
26 4月 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 5701-5706

A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation

M. Sharique, J. Majhi, R. K. Dhungana, L. M. Kammer, M. Krumb, A. Lipp, E. Romero and G. A. Molander, Chem. Sci., 2022, 13, 5701 DOI: 10.1039/D2SC01363K

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