Nickel-catalyzed multi-component coupling reaction of aldimine, alkyne, and dimethylzinc via dimerization of butadiene

Tetrahedron Letters

Volumn 50, Issue 27, 2009, Pages 3982-3984

  Kimura, Masanari ^a   Togawa, Mariko ^a   Tatsuyama, Yasushi ^a   Matsufuji, Kimiko ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Aldimine; Alkyne; Diene; Dimethylzinc; Nickel

Indexed keywords

1,3 BUTADIENE; ALDEHYDE; ALKYNE; AMINE; IMINE; NICKEL; PHOSPHINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; DIMERIZATION; STEREOCHEMISTRY;

EID: 65549164677     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.086     Document Type: Article

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22. Under similar catalytic system, exposure of same amount of p-anisidine (0.5 mmol) and benzylamine (0.5 mmol) to PhCHO (1 mmol) provided a mixture of dienylamine 1a (86%) and trienylamine 2a (76%) (Eq 1). Dienylamine 1a was successfully formed from p-anisidine, whereas trienylamine 2a was produced by benzylamine. This result implies the reaction feature depends on the electrophilicity of aldimine generated from aromatic amine or aliphatic amine as shown in Scheme 2. It seems to rule out the alternative reaction mechanism that amine or the corresponding aldimine acts as a ligand to enhance the nucleophilicity of allylnickel species.{A figure is presented}
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