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Issue 38, 2020
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Dealkoxylation of N-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis

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Abstract

Lewis acid-assisted palladium-catalysed dealkoxylation of N-alkoxyamides has been developed. This reaction proceeded smoothly with a range of N-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.

Graphical abstract: Dealkoxylation of N-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis

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Supplementary files

Article information


Submitted
02 Sep 2020
Accepted
14 Sep 2020
First published
15 Sep 2020

This article is Open Access

Org. Biomol. Chem., 2020,18, 7545-7548
Article type
Communication

Dealkoxylation of N-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis

H. Suzuki, T. Shiomi, K. Yoneoka and T. Matsuda, Org. Biomol. Chem., 2020, 18, 7545
DOI: 10.1039/D0OB01815E

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