Issue 19, 2022
From the journal:

Chemical Science

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

Mohammed Sharique, ORCID logo a   Jadab Majhi, ORCID logo ‡a   Roshan K. Dhungana,‡a   Lisa Marie Kammer, ORCID logo a   Matthias Krumb, ORCID logo a   Alexander Lipp,a   Eugénie Romeroa  and  Gary A. Molander ORCID logo *a  

* Corresponding authors

a Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA
E-mail: gmolandr@sas.upenn.edu

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D2SC01363K
Article type
Edge Article
Submitted
07 Mar 2022
Accepted
09 Apr 2022
First published
26 Apr 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

Permissions

Request permissions

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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