Base Metal Catalysts for Deoxygenative Reduction of Amides to Amines

Research output: Contribution to journalReview article

Abstract

The development of efficient methodologies for production of amines attracts significant attention from synthetic chemists, because amines serve as essential building blocks in the synthesis of many pharmaceuticals, natural products, and agrochemicals. In this regard, deoxygenative reduction of amides to amines by means of transition-metal-catalyzed hydrogenation, hydrosilylation, and hydroboration reactions represents an attractive alternative to conventional wasteful techniques based on stoichiometric reductions of the corresponding amides and imines, and reductive amination of aldehydes with metal hydride reagents. The relatively low electrophilicity of the amide carbonyl group makes this transformation more challenging compared to reduction of other carbonyl compounds, and the majority of the reported catalytic systems employ precious metals such as platinum, rhodium, iridium, and ruthenium. Despite the application of more abundant and environmentally benign base metal (Mn, Fe, Co, and Ni) complexes for deoxygenative reduction of amides have been developed to a lesser extent, such catalytic systems are of great importance. This review is focused on the current achievements in the base-metal-catalyzed deoxygenative hydrogenation, hydrosilylation, and hydroboration of amides to amines. Special attention is paid to the design of base metal catalysts and the mechanisms of such catalytic transformations.
Original languageEnglish
Article number10.3390/catal9060490
Pages (from-to)490
Number of pages27
JournalCatalysts
Volume9
Issue number6
DOIs
Publication statusPublished - May 28 2019

Fingerprint

Amides
amides
Amines
amines
Metals
catalysts
Catalysts
hydroboration
Hydrosilylation
metals
Hydrogenation
hydrogenation
Agrochemicals
Amination
Iridium
Carbonyl compounds
Rhodium
carbonyl compounds
metal hydrides
Imines

Keywords

  • Base metals
  • homogeneous catalysis
  • amides
  • Reduction
  • Hydrogenation
  • hydroboration
  • Hydrosilylation
  • amines

Cite this

Base Metal Catalysts for Deoxygenative Reduction of Amides to Amines. / Khalimon, Andrey; Gudun, Kristina; Hayrapetyan, Davit.

In: Catalysts, Vol. 9, No. 6, 10.3390/catal9060490, 28.05.2019, p. 490.

Research output: Contribution to journalReview article

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