Catalytic Leuckart−Wallach-Type Reductive Amination of Ketones

Kitamura, Masato; Lee, Dong-Hyun; Hayashi, Sotaro; Tanaka, Shinji; Yoshimura, Masahiro

doi:10.1021/jo0203701

Cited by 119 publications

(45 citation statements)

References 13 publications

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“…The reductive alkylation of amines is called the Leuckart-Wallach reaction [112][113][114][115]. The primary or secondary amine reacts with the ketone or aldehyde.…”

Section: Leuckart-wallach and Eschweiler-clarke Reactionsmentioning

confidence: 99%

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Klomp¹,

Hanefeld²,

Peters³

2006

The Handbook of Homogeneous Hydrogenation

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“…The reductive alkylation of amines is called the Leuckart-Wallach reaction [112][113][114][115]. The primary or secondary amine reacts with the ketone or aldehyde.…”

Section: Leuckart-wallach and Eschweiler-clarke Reactionsmentioning

confidence: 99%

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Klomp¹,

Hanefeld²,

Peters³

2006

The Handbook of Homogeneous Hydrogenation

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“…Nevertheless, some useful recent breakthroughs have been achieved [25,26] . A group at Nagoya reported on the use of several metal complexes for the reaction, of which the best proved to be the commercially available [Cp * Rh(III)Cl 2 ] 2 .…”

Section: Asymmetric Reductive Aminations Using Ammonium Formate To Gimentioning

confidence: 99%

Imino Reductions by Transfer Hydrogenation

Wills

2008

Modern Reduction Methods

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11 History and BackgroundIn contrast to ketones, and in particular with respect to asymmetric reductions, the reduction of compounds containing C = N bonds has remained relatively underdeveloped. Some signifi cant breakthroughs have, however, been reported in the last ten years. This chapter will review reductions through metal hydride complexes, " Meerwein -Ponndorf -Verley ( MPV ) type " reductions, and other methods including transfer hydrogenation with organocatalysts and asymmetric LeuckartWallach aminations of ketones. Although there will be discussion of mechanistic aspects, the main focus of this review will be on more recent synthetic applications. The reader ' s attention is also directed to a number of recent useful reviews of this area [1] . Mechanisms of C= N Bond Reduction by Transfer HydrogenationUsing either organic or organometallic catalysts, transfer hydrogenation of imines and other C = N bond -containing substrates, is most commonly carried out using isopropanol, formic acid or a formate salt as the hydrogen source. The most commonly, but not exclusively, used metals are ruthenium, rhodium and iridium.The mechanism of the transfer hydrogenation of imines has been the subject of some extended synthetic, computational and mechanistic studies. The tutorial review by B ä ckvall [1f] provides a very good summary of this. An excellent review by Morris [1c] also contains an incisive overview of hydrogenation and transfer hydrogenation and provides a very logical nomenclature for the possible reduction reaction pathway.The mechanisms that may be considered for imine reduction are the same as for ketone reductions and may be divided into two broad classes (Figure 11.1 ). In the fi rst of these, the MPV reduction or its reverse (Oppenauer oxidation), a metal

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“…Because of the abundance and low price of ammonia, much attention has been focused on its use as a nitrogen source for organic synthesis [4,5]. Recent reports on homogenous catalytic systems using ammonia as the substrate include palladium-catalyzed telomerization of butadiene and ammonia giving primary alkylamines [6], Pd-catalyzed allylic amination [7], copper-and palladiumcatalyzed coupling reactions of ammonia with aryl halides to form arylamines [8][9][10], rhodium-and iridium-catalyzed reductive aminations of carbonyl compounds with ammonium formate and ammonia to afford primary alkylamines [11][12][13] and palladium-catalyzed arylation of ammonia to afford di-and triarylamines [10].…”

Section: Introductionmentioning

confidence: 99%

Direct Synthesis of Secondary Amines From Alcohols and Ammonia Catalyzed by a Ruthenium Pincer Complex

et al. 2014

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Efficient and selective direct synthesis of secondary amines from primary alcohols and ammonia with liberation of water has been achieved, with high turnover numbers and with no generation of waste. In case of benzylic alcohols, imines rather than amines are obtained. This atom economical, environmentally benign reaction is homogenously catalyzed by a well-defined bipyridine based Ru(II)-PNN pincer complex.

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Catalytic Leuckart−Wallach-Type Reductive Amination of Ketones

Cited by 119 publications

References 13 publications

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Transfer Hydrogenation Including the Meerwein‐Ponndorf‐Verley Reduction

Imino Reductions by Transfer Hydrogenation

Direct Synthesis of Secondary Amines From Alcohols and Ammonia Catalyzed by a Ruthenium Pincer Complex

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