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Iron‐Catalyzed Oppenauer‐Type Oxidation of Alcohols
Author(s) -
Coleman Michael G.,
Brown Alec N.,
Bolton Brett A.,
Guan Hairong
Publication year - 2010
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.200900896
Subject(s) - chemistry , dehydrogenation , catalysis , ligand (biochemistry) , alcohol oxidation , cyclopentadienyl complex , hydride , trimethylsilyl , alcohol , organic chemistry , acetone , photochemistry , hydrogen , biochemistry , receptor
A (hydroxycyclopentadienyl)iron dicarbonyl hydride catalyzes the Oppenauer‐type oxidation of alcohols with acetone as the hydrogen acceptor. Many functional groups are tolerant to the oxidation conditions. The same complex also catalyzes the dehydrogenation of diols to lactones. A mechanism involving the formation of iron‐alcohol complexes and their rapid ligand exchange with free alcohols is proposed. The trimethylsilyl groups on the cyclopentadienyl ligand of the catalyst play a critical role in stabilizing the iron hydride and increasing the catalyst lifetime.