NDLI: Simple and Efficient Ruthenium-Catalyzed Oxidation of Primary Alcohols with Molecular Oxygen

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Maiti, Debabrata Lahiri, Goutam Kumar Ray, Ritwika Chandra, Shubhadeep
Description	Author Affiliation: Ray R ( Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India. ritwika@chem.iitb.ac.in.); Chandra S ( Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.); Maiti D ( Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India. dmaiti@chem.iitb.ac.in.); Lahiri GK ( Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India. lahiri@chem.iitb.ac.in.)
Abstract	Oxidative transformations utilizing molecular oxygen $(O_{2})$ as the stoichiometric oxidant are of paramount importance in organic synthesis from ecological and economical perspectives. Alcohol oxidation reactions that employ $O_{2}$ are scarce in homogeneous catalysis and the efficacy of such systems has been constrained by limited substrate scope (most involve secondary alcohol oxidation) or practical factors, such as the need for an excess of base or an additive. Catalytic systems employing $O_{2}$ as the “primary” oxidant, in the absence of any additive, are rare. A solution to this longstanding issue is offered by the development of an efficient ruthenium-catalyzed oxidation protocol, which enables smooth oxidation of a wide variety of primary, as well as secondary benzylic, allylic, heterocyclic, and aliphatic, alcohols with molecular oxygen as the primary oxidant and without any base or hydrogen- or electron-transfer agents. Most importantly, a high degree of selectivity during alcohol oxidation has been predicted for complex settings. Preliminary mechanistic studies including $^{18}O$ labeling established the in situ formation of an oxo–ruthenium intermediate as the active catalytic species in the cycle and involvement of a two-electron hydride transfer in the rate-limiting step.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	26
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-06-20
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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