Stereochemistry of the nickel-catalysed hydrocyanation of olefins

Bäckvall, Jan‐E.; Andell, Ove S.

doi:10.1039/c39810001098

Cited by 25 publications

(12 citation statements)

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“…This resembles the mechanism proposed for transfer hydrogenation of carbonyls1, 15 involving coordination of the substrate to the catalyst and migratory insertion. Isomerization between 14 and 15 has also been observed by Brune et al4e with the Wilkinson catalyst and more recently by Yamagishi et al4b with the active catalyst [RuH 2 (PPh 3 ) 4 ] 16. The transfer hydrogenation of imine 4 using ruthenium amine complex 30 instead of 1 as catalyst (Scheme ) also supports that the reaction proceeds via a ruthenium amine intermediate.…”

Section: Resultssupporting

confidence: 87%

Ruthenium-Catalyzed Transfer Hydrogenation of Imines by Propan-2-ol in Benzene

2002

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Section: Resultssupporting

confidence: 87%

Ruthenium-Catalyzed Transfer Hydrogenation of Imines by Propan-2-ol in Benzene

2002

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“…19 Nucleophilic attack by acetate on (ir-allyl)palladium complexes occurs under mild oxidative conditions. 16,30 In the presence of chloride ligands, acetate attack on 6 in acetic acid occurs exclusively by an external trans attack (Scheme IV). 16 In the absence of chloride ligands the acetate attack occurs exclusively by a cismigration pathway.…”

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confidence: 99%

Palladium in some selective oxidation reactions

Baeckvall¹

1983

Acc. Chem. Res.

275

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“…The nickel(0)-catalyzed reaction of (E)-1-deuterio-3,3-dimethylbut-1-ene with deuterium cyanide was reported by Ba¨ckvall using tetrakis(triphenylphosphite) nickel as catalyst. 20 This study showed that the addition of deuterium and cyanide occurs in a cis fashion.…”

Section: Hydrocyanation Of Other Alkenes and Dienesmentioning

confidence: 92%

Ligand development in the Ni-catalyzed hydrocyanation of alkenes

2010

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The addition of HCN to alkenes is a very useful reaction for the synthesis of functional organic substrates. Industrially the nickel-catalyzed hydrocyanation has gained considerable importance mainly because of the production of adiponitrile in the DuPont process. In this process the hydrocyanation of butadiene is carried out using aryl phosphite-modified nickel catalyst. Since the performance of organo-transition metal complexes is largely determined by the ligand environment of the metal, fundamental understanding and ligand development is of pivotal importance for any progress. This feature article gives an account of the development and application of different mono- and bidentate phosphorus-based ligands in the Ni-catalyzed hydrocyanation reaction of alkenes. Special attention will be paid to the development of insight and understanding of the ligand structural and electronic properties towards the improvement of the catalyst performance in terms of stability, activity, and selectivity.

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Stereochemistry of the nickel-catalysed hydrocyanation of olefins

Cited by 25 publications

References 1 publication

Ruthenium-Catalyzed Transfer Hydrogenation of Imines by Propan-2-ol in Benzene

Ruthenium-Catalyzed Transfer Hydrogenation of Imines by Propan-2-ol in Benzene

Palladium in some selective oxidation reactions

Ligand development in the Ni-catalyzed hydrocyanation of alkenes

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