Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

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

doi:10.1002/ange.201709445

Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

Journal Article · Mon Mar 05 23:00:00 EST 2018 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201709445· OSTI ID:1434866

Wang, Meng ^[1]; ^[1]; ^[1]; ^[2]

Institute for Integrated Catalysis, Pacific Northwest National Laboratory, P.O. Box 999 Richland WA 99352 USA
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

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.

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1434866

Report Number(s):: PNNL-SA-129112; 48810; KC0302010

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 14 Vol. 130; ISSN 0044-8249

Publisher:: German Chemical Society

Country of Publication:: United States

Language:: English

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