Issue 30, 2020

Radical condensation between benzylic alcohols and acetamides to form 3-arylpropanamides

Abstract

A new radical condensation reaction is developed where benzylic alcohols and acetamides are coupled to generate 3-arylpropanamides with water as the only byproduct. The transformation is performed with potassium tert-butoxide as the only additive and gives rise to a variety of 3-arylpropanamides in good yields. The mechanism has been investigated experimentally with labelled substrates, trapping experiments and spectroscopic measurements. The findings indicate a radical pathway where potassium tert-butoxide is believed to serve a dual role as both base and radical initiator. The radical anion of the benzylic alcohol is proposed as the key intermediate, which undergoes coupling with the enolate of the amide to form the new C–C bond. Subsequent elimination to the corresponding cinnamamide and olefin reduction then affords the 3-arylpropanamides.

Graphical abstract: Radical condensation between benzylic alcohols and acetamides to form 3-arylpropanamides

Supplementary files

Article information

Article type
Edge Article
Submitted
25 5 2020
Accepted
24 6 2020
First published
25 6 2020
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., 2020,11, 7800-7806

Radical condensation between benzylic alcohols and acetamides to form 3-arylpropanamides

K. Azizi and R. Madsen, Chem. Sci., 2020, 11, 7800 DOI: 10.1039/D0SC02948C

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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