Author ORCID Identifier

https://orcid.org/0000-0001-7334-9017 : Marcus Muresan

https://orcid.org/0000-0002-1585-5146 : Hariharaputhiran Subramanian

https://orcid.org/0000-0003-1999-4167 : Mukund P. Sibi

https://orcid.org/0000-0003-2334-4503 : James R. Green

Document Type

Article

Publication Date

6-15-2021

Publication Title

European Journal of Organic Chemistry

Volume

2021

Issue

22

First Page

3359

Keywords

Alkyne, Allene, Propargyl, Radicals, Synthetic methods

Last Page

3375

Abstract

The appearance of propargyl radicals as synthetic intermediates has increased in recent years from a structural curiosity to a frequent occurrence. This minireview covers the synthetically relevant organic chemistry involving the intermediacy of propargyl radicals. The review is organized by the process employed in radical generation, including H-atom abstraction, propargyl-X homolyses, radical addition to enynes, reduction of polar C=X bonds, reductions of stable carbocations, and metal-mediated coupling reactions. The relevant mechanisms of generation and reaction are discussed, as are applications in syntheses of target molecules of interest.

DOI

10.1002/ejoc.202100367

Funding Reference Number

NSERC, RGPIN-2016-04946

Comments

This is the peer reviewed version of the following article:

Muresan, M.; Subramanian, H.; Sibi, M. P.*; Green, J. R.* (2021) Propargyl Radicals in Organic Synthesis, Eur. J. Org. Chem., 3359-3375.

This has been published in final form at https://doi.org/10.1002/ejoc.202100367.

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