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Shvo's Catalyst in Hydrogen Transfer Reactions
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2011 (English)In: BIFUNCTIONAL MOLECULAR CATALYSIS, 2011, 85-125 p.Conference paper (Refereed)
Abstract [en]

This chapter reviews the use of Shvo's catalyst in various hydrogen transfer reactions and also discusses the mechanism of the hydrogen transfer. The Shvo catalyst is very mild to use since no activation by base is required in the transfer hydrogenation of ketones or imines or in the transfer dehydrogenation of alcohols and amines. The Shvo catalyst has also been used as an efficient racemization catalyst for alcohols and amines. Many applications of the racemization reaction are found in the combination with enzymatic resolution leading to a dynamic kinetic resolution (DKR). In these dynamic resolutions, the yield based on the starting material can theoretically reach 100%. The mechanism of the hydrogen transfer from the Shvo catalyst to ketones (aldehydes) and imines as well as the dehydrogenation of alcohols and amines has been studied in detail over the past decade. It has been found that for ketones (aldehydes) and alcohols, there is a concerted transfer of the two hydrogens involved, whereas for typical amines and imines, there is a stepwise transfer of the two hydrogens. One important question is whether the substrate is coordinated to the metal or not in the hydrogen transfer step(s). The pathway involving coordination to activate the substrate is called the inner-sphere mechanism, whereas transfer of hydrogen without coordination is called the outer-sphere mechanism. These mechanistic proposals together with experimental and theoretical studies are discussed.

Place, publisher, year, edition, pages
2011. 85-125 p.
, Topics in Organometallic Chemistry, ISSN 1436-6002 ; 37
Keyword [en]
Dynamic kinetic asymmetric transformation (DYKAT), Dynamic kinetic resolution (DKR), Hydrogenation, Imine reduction, Ketone reduction, Mechanism of carbonyl reduction, Mechanism of imine reduction, Mechanism of dihydrogen activation, Ruthenium catalysis, Shvo's catalyst, Transfer hydrogenation
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-66623DOI: 10.1007/3418_2011_7ISI: 000293421100004ISBN: 978-3-642-20730-3OAI: diva2:468645
authorCount :3Available from: 2011-12-21 Created: 2011-12-20 Last updated: 2011-12-21Bibliographically approved

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Warner, Madeleine C.Bäckvall, Jan-E.
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