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

Last Page

3375

DOI

10.1002/ejoc.202100367

Keywords

Alkyne, Allene, Propargyl, Radicals, Synthetic methods

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.

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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Available for download on Friday, August 19, 2022

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