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Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

Prasad M. Kathe, Andreas Berkefeld, Ivana Fleischer*

*Eberhard Karls University Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany, Email:

P. M. Kathe, A. Berkefeld, I. Fleischer, Synlett, 2021, 32, 1629-1632.

DOI: 10.1055/s-0040-1706683

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A combination of a Ni-H precatalyst and excess Brĝnsted acid enables a deallylation of O- and N-allyl functional groups. Key steps are a Ni-catalyzed double-bond migration of the O- and N-allyl group followed by Brĝnsted acid induced O/N-C bond hydrolysis. This deprotection method tolerates a broad range of functional groups.

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Key Words

deprotection of allylic ethers, nickel catalysis, isomerization

ID: J72-Y2021