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Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes

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Abstract

An efficient Pd-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes was developed. Instead of affording the Sonogashira coupling products, the protocol provided a series of β,γ-alkenyl carboxamides which were subsequently subjected to catalytic hydrogenation to give the corresponding α,α-dialkyl carboxamides. A preliminary mechanistic study revealed a radical coupling process and the solvent served as the hydrogen source. The judicious selection of a base, Pd catalyst and solvent was critical for the success of the reaction.

Graphical abstract: Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes

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Supplementary files

Article information


Submitted
22 Aug 2020
Accepted
29 Sep 2020
First published
30 Sep 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Palladium-catalyzed reductive cross-coupling between α-bromo carboxamides and terminal alkynes

M. A. Aliyu, B. Li, H. Yang and W. Tang, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO01013H

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