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Title: Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

Abstract

Pd/C catalyzes C-O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by methanol in H2. The aromatic C-O bond is cleaved by reductive methanolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with methanol to form a ketal, which generates methoxycyclohexene by eliminating phenol or an alkanol. Subsequent hydrogenation leads to methoxycyclohexane.

Authors:
 [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]
  1. Institute for Integrated Catalysis, Pacific Northwest National Laboratory, P.O. Box 999 Richland WA 99352 USA
  2. Institute for Integrated Catalysis, Pacific Northwest National Laboratory, P.O. Box 999 Richland WA 99352 USA; Department of Chemistry and Catalysis Research Institute, TU München, Lichtenbergstrasse 4 85748 Garching Germany
Publication Date:
Research Org.:
Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)
Sponsoring Org.:
USDOE
OSTI Identifier:
1434866
Report Number(s):
PNNL-SA-129112
Journal ID: ISSN 0044-8249; 48810; KC0302010
DOE Contract Number:  
AC05-76RL01830
Resource Type:
Journal Article
Resource Relation:
Journal Name: Angewandte Chemie; Journal Volume: 130; Journal Issue: 14; Related Information: 3809-3813
Country of Publication:
United States
Language:
English
Subject:
aryl ether; hydrogenation; palladium; methanolysis; selective cleavage; Environmental Molecular Sciences Laboratory

Citation Formats

Wang, Meng, Gutiérrez, Oliver Y., Camaioni, Donald M., and Lercher, Johannes A.. Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds. United States: N. p., 2018. Web. doi:10.1002/ange.201709445.
Wang, Meng, Gutiérrez, Oliver Y., Camaioni, Donald M., & Lercher, Johannes A.. Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds. United States. doi:10.1002/ange.201709445.
Wang, Meng, Gutiérrez, Oliver Y., Camaioni, Donald M., and Lercher, Johannes A.. Tue . "Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds". United States. doi:10.1002/ange.201709445.
@article{osti_1434866,
title = {Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds},
author = {Wang, Meng and Gutiérrez, Oliver Y. and Camaioni, Donald M. and Lercher, Johannes A.},
abstractNote = {Pd/C catalyzes C-O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by methanol in H2. The aromatic C-O bond is cleaved by reductive methanolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with methanol to form a ketal, which generates methoxycyclohexene by eliminating phenol or an alkanol. Subsequent hydrogenation leads to methoxycyclohexane.},
doi = {10.1002/ange.201709445},
journal = {Angewandte Chemie},
number = 14,
volume = 130,
place = {United States},
year = {Tue Mar 06 00:00:00 EST 2018},
month = {Tue Mar 06 00:00:00 EST 2018}
}