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:1423913

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

Abstract

Palladium on carbon catalyzes C−O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by alcohols (R−OH) in H ₂ . 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.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

OSTI ID:: 1423913

Alternate ID(s):: OSTI ID: 1434866
OSTI ID: 1598824

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

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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