950188-56-4

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 100-60-7 N-methylcyclohexylamine 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 14579-95-4 N-(trimethylsilylmethyl)cyclohexylamine 

Downstream Products

• 4833-43-6 N,N'-Dicyclohexyl-N,N'-dimethyl-N''-phenyl-guanidine 
• 20550-63-4 -trimethylsilan 
• 32552-30-0 2-(cyclohexyl-methyl-amino)-6-phenyl-[1,3,5]oxadiazin-4-one 
• 32552-23-1 C₁₈H₂₈N₂O₂Si 
• 1040402-56-9 N-p-tosyl-2-[(cyclohexyl)methylamino]benzhydrylamine 

Relevant academic research and scientific papers

Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination

This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes of organic electrophiles. The synthetic value of this process is demonstrated by a single-step synthesis of antimigraine drug flunarizine (Sibelium) and high yielding derivatization of paroxetine (Paxil) and metoprolol (Lopressor). Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation. Accordingly, application of catalytic conditions to an intramolecular reductive coupling is demonstrated for the synthesis of endo- and exocyclic benzhydryl amines.

Three-component coupling using arynes and aminosilanes for ortho-selective double functionalization of aromatic skeletons

(Chemical Equation Presented) Arynes were found to couple with aminosilanes and carbonyl compounds in the presence of benzoic acid to provide 2-aminobenzhydrols. Sulfonylimines could also be applied to the reaction, enabling amino and aminomethyl moieties to be incorporated into contiguous positions of aromatic skeletons. Only a small amount of the three-component coupling product was obtained in the absence of benzoic acid, which confirms its vital role in the present reaction.

Three-component coupling of arynes, aminosilanes, and aldehydes

A three-component coupling of arynes, aminosilanes, and aldehydes enables diverse amino and hydroxymethyl groups to be incorporated directly into 1,2-positions of aromatic rings.