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Palladium‐Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds
Author(s) -
Wang Meng,
Gutiérrez Oliver Y.,
Camaioni Donald M.,
Lercher Johannes A.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201709445
Subject(s) - chemistry , ether , palladium , aryl , catalysis , medicinal chemistry , solvolysis , diphenyl ether , enol , enol ether , bond cleavage , organic chemistry , hydrolysis , alkyl
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.