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Trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives.

ABSTRACT: A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a commercially available heterogeneous palladium catalyst is reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite cis-isomers. The diastereoselectivity of the phenol hydrogenation can be switched to the cis-isomers by employing rhodium-based catalysts. Moreover, a protocol for the chemoselective hydrogenation of phenols to cyclohexanones was developed.

SUBMITTER: Wollenburg M

PROVIDER: S-EPMC7594304 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives.

Wollenburg Marco M Heusler Arne A Bergander Klaus K Glorius Frank F

ACS catalysis 20200915 19

A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a commercially available heterogeneous palladium catalyst is reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite c ...[more]

PMID: 33133752

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