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

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 coul...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 38; pp. 7545 - 7548
Main Authors Suzuki, Hirotsugu, Shiomi, Takahiro, Yoneoka, Kenji, Matsuda, Takanori
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 07.10.2020
Subjects
Catalysis
Hydrogen storage
Lewis acid
Palladium
Reducing agents
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Summary: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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01815e