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Vanadium‐Catalyzed Oxidative Debenzylation of O ‐Benzyl Ethers at ppm Level
Author(s) -
Urgoitia Garazi,
SanMartin Raul,
Herrero María Teresa,
Domínguez Esther
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600593
Subject(s) - chemistry , catalysis , vanadium , pincer movement , alkoxy group , alkyne , ether , oxidative phosphorylation , alkene , acetal , benzyl alcohol , organic chemistry , pincer ligand , combinatorial chemistry , medicinal chemistry , biochemistry , alkyl
An advantageous methodology for the oxidative debenzylation of ethers has been developed. Very low amounts of a catalyst system based on vanadyl acetylacetonate and a triazole type pincer ligand allow the selective oxidative cleavage of a number of O ‐benzyl ethers in the presence of oxygen as the sole oxidant. The methodology tolerates a number of functional groups such as halo‐, alkoxy‐, or trifluoromethylarenes, alkyne, alkene, ether, and acetal units. Large‐scale deprotections can be also carried out by the optimized procedure, which is amenable to enantioenriched reactants as well.