Issue 35, 2023

Azido-alkynylation of alkenes through radical-polar crossover

Abstract

We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design of a photocatalytic redox-neutral radical polar crossover process was key to develop this transformation. A variety of homopropargylic azides possessing electron-rich and -poor aryls, heterocycles or ether substituents could be accessed in 34–84% yield. The products are synthetically useful building blocks that could be easily transformed into pyrroles or bioactive amines.

Graphical abstract: Azido-alkynylation of alkenes through radical-polar crossover

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Article information

Article type
Edge Article
Submitted
29 Jun 2023
Accepted
10 Aug 2023
First published
11 Aug 2023
This article is Open Access

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

Chem. Sci., 2023,14, 9452-9460

Azido-alkynylation of alkenes through radical-polar crossover

J. Borrel and J. Waser, Chem. Sci., 2023, 14, 9452 DOI: 10.1039/D3SC03309K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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