74910-03-5

Basic information

• Product Name: [Ni(η2-benzaldehyde)(PCy3)2]
• Synonyms: [Ni(η2-benzaldehyde)(PCy3)2]
• CAS NO: 74910-03-5
• Molecular Weight: 725.682
• Mol File: 74910-03-5.mol

Chemical Properties

• CAS DataBase Reference: [Ni(η2-benzaldehyde)(PCy3)2](CAS DataBase Reference)
• NIST Chemistry Reference: [Ni(η2-benzaldehyde)(PCy3)2](74910-03-5)
• EPA Substance Registry System: [Ni(η2-benzaldehyde)(PCy3)2](74910-03-5)

Safety Data

• Hazardous Substances Data: 74910-03-5(Hazardous Substances Data)

Upstream product

• 41685-59-0 ethene-bis(tricyclohexylphosphane)-nickel(0) 
• 100-52-7 benzaldehyde 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 
• 501-65-5 diphenyl acetylene 
• 2622-14-2 tricyclohexylphosphine 

Downstream Products

• 907606-54-6 [(η1:η1-Me3SiOCH(Ph)Ni(PCy3)OTf] 
• 1256779-00-6 [Ni(0)(η2-benzaldehyde-AlMe2(trifluoromethanesulfonate))(PCy3)2] 
• 1256778-99-0 [Ni(C(Ph)C(Ph)CH(Ph)O)(PCy₃)AlMe₂(trifluoromethanesulfonate)] 

Relevant articles and documents

Intermediacy of Ni-Ni Species in sp2 C-O Bond Cleavage of Aryl Esters: Relevance in Catalytic C-Si Bond Formation

Monodentate phosphine ligands are frequently employed in the Ni-catalyzed C-O functionalization of aryl esters. However, the extensive body of preparative work on such reactions contrasts with the lack of information concerning the structure and reactivity of the relevant nickel intermediates. In fact, experimental evidence for a seemingly trivial oxidative addition into the C-O bond of aryl esters with monodentate phosphines and low-valent nickel complexes still remains elusive. Herein, we report a combined experimental and theoretical study on the Ni(0)/PCy3-catalyzed silylation of aryl pivalates with CuF2/CsF additives that reveals the involvement of unorthodox dinickel oxidative addition complexes in C-O bond cleavage and their relevance in C-Si bond formation. We have obtained a mechanistic picture that clarifies the role of the additives and demonstrates that dinickel complexes act as reservoirs of the propagating monomeric nickel complexes by disproportionation. We believe this study will serve as a useful entry point to unravelling the mechanistic underpinnings of other related Ni-catalyzed C-O functionalization reactions employing monodentate phosphines.

Nickel(0)-catalyzed formation of oxaaluminacyclopentenes via an oxanickelacyclopentene key intermediate: Me2AlOTf-assisted oxidative cyclization of an aldehyde and an alkyne with nickel(0)

The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an oxanickelacyclopentene, the structure of which was unambiguously determined

REAKTIONEN VON HETEROOLEFINEN AN ZENTRALMETALLEN IN NIEDRIGEN OXIDATIONSSTUFEN: STABILE ALDEHYDKOMPLEXE DES NICKEL(0) UND VERWANDTE VERBINDUNGEN

Nickel(0) complex moieties with a high electron density at the central atom are able to yield stable complexes with many aromatic aldehydes. 1H NMR spectroscopic data give evidence about olefin-like bonding of the aldehyde group and indicate a high charge transfer.Chelate ligands like tetramethylethylenediamine yield stable complexes of the composition (TME)NiL (L = aldehyde, benzil, α,β-unsaturated carbonyl compounds).Some reactions and properties of typical mixed ligand complexes are described.