Platinum catalysed hydrolytic amidation of unactivated nitriles

Cobley, Christopher J.; Heuvel, Marco van den; Abbadi, A.; Vries, Johannes G. de

doi:10.1016/s0040-4039(00)00181-7

Cited by 112 publications

(48 citation statements)

References 11 publications

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“…Using this complex, other amide-bond forming reactions could be developed. In this context, de Vries and co-workers found that 1 efficiently catalyzes the direct conversion of unactivated nitriles to N-substituted amides by reaction with both primary and secondary amines in the presence of water (Scheme 18) [77]. A mechanism involving the initial formation of an amidine intermediate, which subsequently hydrolyzes into the amide, was proposed.…”

Section: Other Synthetic Applications Of Complex [Pth{(pme 2 O) 2 H}(mentioning

confidence: 99%

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Cadierno

2015

Applied Sciences

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Abstract:The air-stable hydride-platinum(II) complex [PtH{(PMe2O)2H}(PMe2OH)], reported by Parkins and co-workers in 1995, is the most versatile catalyst currently available for the hydration of C≡N bonds. It features remarkable activity under relatively mild conditions and exceptionally high functional group compatibility, facts that have allowed the implementation of this complex in the synthesis of a large number of structurally complex, biologically active molecules and natural products. In this contribution, synthetic applications of the Parkins catalyst are reviewed.

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Section: Other Synthetic Applications Of Complex [Pth{(pme 2 O) 2 H}(mentioning

confidence: 99%

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Cadierno

2015

Applied Sciences

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“…Mechanistic studies by Duchateau and co-workers, employing the [RuH 2 (PPh 3 ) 4 ]-catalyzed hydrolytic amidation of pentanenitrile with n-hexylamine as model reaction, pointed out that the process proceeds through the initial hydration of the nitrile to form an intermediate primary amide, which subsequently reacts with the amine to give the final N-substituted amide product (parth (a) in Scheme 14) [79]. This reaction pathway contrasts with that commonly proposed for other homogeneous metal catalysts (Pt-, Cu-Zn-or Fe-based systems) where an amidine intermediate, which evolves into the final amide product by hydrolysis, is initially formed (parth (b) in Scheme 14) [71,73,[75][76][77]. …”

Section: Ruthenium-catalyzed Hydrolytic Amidation Of Nitriles With Ammentioning

confidence: 92%

“…In this context, although little studied, the catalytic amidation of nitriles with amines in the presence of water has emerged in recent years as a useful tool for the straightforward generation of secondary and tertiary amides (Scheme 10) [71][72][73][74][75][76][77]. This amidation reaction was reported for the first time by Murahashi and coworkers in 1986 using the unique ruthenium catalyst described so far for this catalytic transformation [78].…”

Section: Ruthenium-catalyzed Hydrolytic Amidation Of Nitriles With Ammentioning

confidence: 99%

Ruthenium-Catalyzed Amide-Bond Formation

Crochet

Cadierno

2014

Ruthenium in Catalysis

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The amide functionality is one of the most important functional groups in organic and biological chemistry. Classical synthetic strategies of amides involve the stoichiometric, and poor atom efficient, reaction of amines with carboxylic acid derivatives. Transition-metal-catalyzed reactions have emerged in recent years as more atom-economical and powerful tools for preparing amides, opening previously unavailable routes from substrates other than the carboxylic acids and their derivatives. Ruthenium-based catalysts have been at the heart of these advances, and this chapter pretends to give an overview of the field. Among others, the following ruthenium-catalyzed synthetic approaches of amides will be discussed: the hydration of nitriles, the hydrolytic amidation of nitriles with amines, the rearrangement of aldoximes, the coupling of aldehydes with hydroxylamine, and the dehydrogenative amidation of alcohols, aldehydes and esters.

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“…13 Achiral or racemic secondary phosphine oxides have been used as ligands in the platinum-catalyzed hydroformylation, 14 the hydrolysis, 15 and amination of nitriles 16 and in Pd-catalyzed coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

The application of monodentate secondary phosphine oxide ligands in rhodium- and iridium-catalyzed asymmetric hydrogenation

Jiang

Berg

Minnaard

et al. 2004

Tetrahedron: Asymmetry

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The application of monodentate secondary phosphine oxide ligands in rhodium-and iridiumcatalyzed asymmetric hydrogenation Jiang, Xiao-bin; van den Berg, Michel; Minnaard, Adriaan; de Vries, Johannes G.; Feringa, B.L. Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Abstract-Enantiopure secondary phosphine oxides have been tested as ligands in the rhodium-and iridium-catalyzed asymmetric hydrogenation of functionalized olefins. tert-Butylphosphinoyl benzene turned out to be a versatile ligand in the iridium-catalyzed hydrogenation of b-branched dehydroamino esters and in the rhodium-catalyzed hydrogenation of an enol carbamate.

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Platinum catalysed hydrolytic amidation of unactivated nitriles

Cited by 112 publications

References 11 publications

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Ruthenium-Catalyzed Amide-Bond Formation

The application of monodentate secondary phosphine oxide ligands in rhodium- and iridium-catalyzed asymmetric hydrogenation

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