Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

Meng Wang; Oliver Y. Gutiérrez; Donald M. Camaioni; Johannes A. Lercher

doi:10.1002/anie.201709445

Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

Meng Wang, Oliver Y. Gutiérrez, Donald M. Camaioni, Johannes A. Lercher

Chair of Chemical Technology II

Pacific Northwest National Laboratory

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

Palladium on carbon catalyzes C−O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by alcohols (R−OH) in H₂. The aromatic C−O bond is cleaved by reductive solvolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with alcohols to form a ketal, which generates 1-cyclohexenyl−O−R by eliminating phenol or an alkanol. Subsequent hydrogenation leads to cyclohexyl−O−R.

Original language	English
Pages (from-to)	3747-3751
Number of pages	5
Journal	Angewandte Chemie International Edition in English
Volume	57
Issue number	14
DOIs	https://doi.org/10.1002/anie.201709445
State	Published - 26 Mar 2018

Keywords

aryl ethers
hydrogenation
methanolysis
palladium
selective bond cleavage

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abstract = "Palladium on carbon catalyzes C−O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by alcohols (R−OH) in H2. The aromatic C−O bond is cleaved by reductive solvolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with alcohols to form a ketal, which generates 1-cyclohexenyl−O−R by eliminating phenol or an alkanol. Subsequent hydrogenation leads to cyclohexyl−O−R.",

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AU - Wang, Meng

AU - Gutiérrez, Oliver Y.

AU - Camaioni, Donald M.

AU - Lercher, Johannes A.

PY - 2018/3/26

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N2 - Palladium on carbon catalyzes C−O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by alcohols (R−OH) in H2. The aromatic C−O bond is cleaved by reductive solvolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with alcohols to form a ketal, which generates 1-cyclohexenyl−O−R by eliminating phenol or an alkanol. Subsequent hydrogenation leads to cyclohexyl−O−R.

AB - Palladium on carbon catalyzes C−O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by alcohols (R−OH) in H2. The aromatic C−O bond is cleaved by reductive solvolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with alcohols to form a ketal, which generates 1-cyclohexenyl−O−R by eliminating phenol or an alkanol. Subsequent hydrogenation leads to cyclohexyl−O−R.

KW - aryl ethers

KW - hydrogenation

KW - methanolysis

KW - palladium

KW - selective bond cleavage

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JO - Angewandte Chemie International Edition in English

JF - Angewandte Chemie International Edition in English

IS - 14

ER -

Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

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