Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds

Journal Article · Mon Mar 26 00:00:00 EDT 2018 · Angewandte Chemie International Edition

DOI:https://doi.org/10.1002/ange.201709445· OSTI ID:1598824

Wang, Meng  ^[1]; Gutierrez-Tinoco, Oliver Y.  ^[1]; Camaioni, Donald M.  ^[1]; Lercher, Johannes A.  ^[1]

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1. BATTELLE (PACIFIC NW LAB)

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 Lab. (PNNL), Richland, WA (United States)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC05-76RL01830
• OSTI ID: 1598824
• Report Number(s): PNNL-SA-129112
• Journal Information: Angewandte Chemie International Edition, Vol. 130, Issue 14
• Country of Publication: United States
• Language: English

Related Subjects

aryl ether
hydrogenation
palladium
methanolysis
selective cleavage