Catalytic Amination of Alcohols, Aldehydes, and Ketones

Klyuev, M. V.; Khidekel, M. L.

doi:10.1070/rc1980v049n01abeh002442

Cited by 72 publications

(28 citation statements)

References 4 publications

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“…With regards to the nature of the catalyst, several examples on the performance of various supported metals can be found in reviews [4][5][6][7][12][13][14][15]. In addition to the metallic component, the support has also a considerable influence on the rate and direction of amination.…”

Section: Methodsmentioning

confidence: 99%

“…Herein is provided a brief review covering the main features of the method; further information, including numerous examples, can be found in the pertinent literature [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16].…”

Section: Amination Of Alcoholsmentioning

confidence: 99%

“…An industrial method for phenol amination applies acidic oxide catalysts, such as Al 2 O 3 and SiO 2 -Al 2 O 3 , at temperatures up to 500 • C and moderate to high pressure [5,7,14,15,33,[54][55][56]. Aniline is the main product (85-99% yield) at high ammonia excess, with diphenylamine and carbazole as typical byproducts.…”

Section: Amination Of Phenolsmentioning

confidence: 99%

“…It is used on an industrial scale in preference to alcohol amination when the aldehyde or ketone is cheap (acetone and lower aldehydes manufactured by the oxo synthesis) [6]. Further examples can be found for small-scale applications in fine and pharmaceutical chemistry [2,5,11,[59][60][61][62][63]. Applications of reductive alkylation in enantioselective organic synthesis (see Section 14.12.3.6) or as part of multicomponent coupling reactions [64] have also been reported.…”

Section: Amination Of Carbonyl Compounds (Reductive Alkylation)mentioning

confidence: 99%

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Amination Reactions

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Baiker

Kleist

et al. 2008

Handbook of Heterogeneous Catalysis

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The sections in this article are Introduction Amination of Alcohols Aliphatic Alcohols Amination over Metal Catalysts (Dehydrogenation Route) Amination over Solid Acid Catalysts (Dehydration Route) Amino Alcohols, Polyalcohols Amination of Phenols Amination of Carbonyl Compounds (Reductive Alkylation) Reaction Mechanism Catalysts, Reaction Conditions Selective Synthesis of Primary, Secondary, or Tertiary Amines Amination with Bifunctional Amines or Carbonyl Compounds Heterocyclic Ring Formation Stereoselectivity Amination of Carboxylic Acids and Esters Amination of Alkenes and Alkynes (Hydroamination) Amination of Ethers Amination of Halogen Compounds Amination of Haloalkanes Amination of Haloaryls Amination of Hydrocarbons Amination of Carbon Monoxide and Carbon Dioxide

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Section: Methodsmentioning

confidence: 99%

Section: Amination Of Alcoholsmentioning

confidence: 99%

Section: Amination Of Phenolsmentioning

confidence: 99%

Section: Amination Of Carbonyl Compounds (Reductive Alkylation)mentioning

confidence: 99%

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Amination Reactions

Mallát

Baiker

Kleist

et al. 2008

Handbook of Heterogeneous Catalysis

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“…[14] In 1981, Grigg and co-workers reported homogeneous catalysts for the amination of alcohols using rhodium-, iridium-and ruthenium-based catalysts, [15] and other metals have also been used in this transformation. [16] Jonathan Several ruthenium catalysts have been used for the formation of secondary amines from primary amines and alcohols, although the reaction conditions are often harsh. Typical reactions, as shown in Scheme 3, include the use of RuCl 2 A C H T U N G T R E N N U N G (PPh 3 ) 3 in the alkylation of aniline 1 which gave secondary amines 2 as the major product along with some tertiary amine arising from di-alkylation.…”

Section: Amination Of Alcoholsmentioning

confidence: 99%

Borrowing Hydrogen in the Activation of Alcohols

2007

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Alcohols can be temporarily converted into carbonyl compounds by the metal-catalysed removal of hydrogen. The carbonyl compounds are reactive in a wider range of transformations than the precursor alcohols and can react in situ to give imines, alkenes, and a-functionalised carbonyl compounds. The metal catalyst, which had borrowed the hydrogen, then returns it to the transformed carbonyl compound, leading to an overall process in which alcohols can be converted into amines, compounds containing C À C bonds and b-functionalised alcohols.

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Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

2002

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Reductive amination is an important tool for synthetic organic chemists in the construction of carbon‐nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent. A wide variety of substrates can be used including aliphatic and aromatic aldehydes and ketones, and even benzophenones. A range of amines from ammonia to aromatic amines, including those with electron‐withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful. This chapter focuses on those conditions in which the carbonyl component, amine, and reducing reagent react in the same vessel. This review is restricted to reductive aminations using borohydride and borane reducing agents. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron‐containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced, through the middle of 1999. In addition to reductive aminations of aldehyde and ketone substrates, reactions of related structures including acetals, aminals, ketals, carboxylic acids, nitriles, and dicarbonyls that form a nitrogen‐containing ring are reviewed. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. The intramolecular variant is a useful method for preparing cyclic amines. All of the various boron‐containing hydride sources in reductive aminations, including labeled metal hydrides, are reviewed. Instances of reductive aminations that failed are described. Applications of this method to a solid support in parallel synthesis in combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as reductive lactamizations are discussed.

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Catalytic Amination of Alcohols, Aldehydes, and Ketones

Cited by 72 publications

References 4 publications

Amination Reactions

Amination Reactions

Borrowing Hydrogen in the Activation of Alcohols

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

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