86774-89-2

Upstream product

• 536-74-3 phenylacetylene 
• 103-67-3 benzyl-methyl-amine 
• 98-81-7 1-bromovinylbenzene 
• 618-34-8 1-chlorostyrene 

Downstream Products

• 10419-51-9 N-benzyl-N-α-phenylethyl-p-toluidine 

Relevant academic research and scientific papers

Palladium-Catalyzed Cross-Coupling Reactions of Amines with Alkenyl Bromides: A New Method for the Synthesis of Enamines and Imines

The palladium-catalyzed cross-coupling reaction of alkenyl bromides with secondary and primary amines gives rise to enamines and imines, respectively. This new transformation expands the applicability of palladium-catalyzed C-N bond forming reactions (the Buchwald-Hartwig amination), which have mostly been applied to aryl halides. After screening of different ligands, bases, and solvents, the catalytic combination [Pd2(dba)3]/BINAP in the presence of NaOtBu in toluene gave the best results in the cross-coupling of secondary amines with 1-bromostyrene (dba=dibenzylideneacetone, BINAP=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl). The corresponding enamines are obtained cleanly and in nearly quantitative yields. However, steric hindrance seems to be a limitation of the reaction, as amines carrying large substituents are not well converted. The same methodology can be applied to the coupling of secondary amines with 2-bromostyrene. Moreover, the reaction with substituted 2-bromopropenes allows regioselective synthesis of isomerizable terminal enamines without isomerization of the double bond. The best catalytic conditions for the cross-coupling of 1-bromostyrene with primary amines include again the use of the Pd°/BINAP/NaOtBu system. The reaction gives rise to the expected imines in very short times and with low catalyst loadings. A set of structurally diverse imines can be prepared by this methodology through variations in the structure of both coupling partners. However, 2-bromostyrene failed to give good results in this coupling reaction, probably due to product inhibition of the catalytic cycle. Competition experiments of vinyl versus aryl amination reveal that the reaction occurs preferentially on vinyl bromides.

Palladium catalyzed animation of vinyl chlorides: A new entry to imines, enamines and 2-amino-1,3-butadienes

Vinyl chlorides are employed for the first time in palladium catalyzed cross-coupling reactions with amines to furnish imines and enamines. The new methodology has been applied to the synthesis of 2-amino-1,3-butadienes, that could not be achieved from th

Novel method for the synthesis of enamines by palladium catalyzed amination of alkenyl bromides

The intermolecular palladium catalyzed cross-coupling reaction between secondary amines and alkenyl bromides is described for the first time, giving rise to enamines with very high yields and regioselectivity.

Alkynylmercury Chloride or Acetate as Intermediates in the Mercury(II) Salt-promoted Addition of Aliphatic and Aromatic Amines to Terminal Acetylenes

Arylaminomercuriation of terminal acetylenes has been carried out with aliphatic amines to yield amines and enamines.Phenylethynylmercury chloride is shown to be an intermediate in the mercury(II) salt-promoted addition of aliphatic and aromatic amines to terminal alkynes.