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Issue 30, 2020
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Radical condensation between benzylic alcohols and acetamides to form 3-arylpropanamides

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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

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Supplementary files

Article information


Submitted
25 May 2020
Accepted
24 Jun 2020
First published
25 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 7800-7806
Article type
Edge Article

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

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