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

33 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
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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title = "Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds",

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.",

keywords = "aryl ethers, hydrogenation, methanolysis, palladium, selective bond cleavage",

author = "Meng Wang and Guti{\'e}rrez, \{Oliver Y.\} and Camaioni, \{Donald M.\} and Lercher, \{Johannes A.\}",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/anie.201709445",

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T1 - Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

AU - Wang, Meng

AU - Gutiérrez, Oliver Y.

AU - Camaioni, Donald M.

AU - Lercher, Johannes A.

PY - 2018/3/26

Y1 - 2018/3/26

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

UR - https://www.scopus.com/pages/publications/85043323151

U2 - 10.1002/anie.201709445

DO - 10.1002/anie.201709445

M3 - Article

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AN - SCOPUS:85043323151

SN - 1433-7851

VL - 57

SP - 3747

EP - 3751

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 14

ER -

Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

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Keywords

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