Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

Prasad M. Kathe; Andreas Berkefeld; Ivana Fleischer

doi:10.1055/s-0040-1706683

Synlett, Table of Contents

Synlett 2021; 32(16): 1629-1632
DOI: 10.1055/s-0040-1706683

cluster

Modern Nickel-Catalyzed Reactions

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

Prasad M. Kathe

^aInstitute of Organic Chemistry, Faculty of Science and Mathematics, Eberhard Karls University Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

,

Andreas Berkefeld∗

^bInstitute of Inorganic Chemistry, Faculty of Science and Mathematics, Eberhard Karls University Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

,

Ivana Fleischer ∗

^aInstitute of Organic Chemistry, Faculty of Science and Mathematics, Eberhard Karls University Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

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Abstract

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Abstract

This report discloses the deallylation of O- and N-allyl functional groups by using a combination of a Ni-H precatalyst and excess Brønsted acid. Key steps are the isomerization of the O- or N-allyl group through Ni-catalyzed double-bond migration followed by Brønsted acid induced O/N–C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Key words

nickel catalysis - deprotection - allylic ethers - isomerization - selectivity

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References

References and Notes

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