34163-22-9

Upstream product

• 571-58-4 1,4-dimethylnaphthalene 
• 98-88-4 benzoyl chloride 
• 140-29-4 phenylacetonitrile 
• 5261-50-7 1-(chloromethyl)-4-methylnaphthalene 

Downstream Products

• 37620-34-1 2-((E)-1,2-Diphenyl-vinyl)-1,4-dimethyl-naphthalene 
• 37620-33-0 2-((Z)-1,2-Diphenyl-vinyl)-1,4-dimethyl-naphthalene 
• 37620-32-9 1-(1,4-Dimethyl-naphthalen-2-yl)-1,2-diphenyl-ethanol 

Relevant academic research and scientific papers

Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic Aromatic Substitution of 1-(Chloromethyl)naphthalenes with Arylacetonitriles

The palladium-catalyzed reaction of 1-(chloromethyl)naphthalenes 1 with (hetero)arylacetonitriles 2 gives either para- or ortho-acylated naphthalenes (3 or 4) in good to high yields. The regioselectivity can be controlled by the ligand of a palladium catalyst. A sterically bulky ligand, tBuPPh2, affords para-acylated products 3, whereas a sterically less bulky ligand, Me2PPh, provides ortho-acylated products 4. Further, direct substitution product 5 at the benzylic position is not obtained essentially, although such a reaction at the benzylic position is favorable in ordinary nucleophilic substitutions. In this paper, it was revealed that the benzylpalladium intermediate could react through a different mode (η3-benzylpalladium intermediate or η1-benzylpalladium intermediate) in nucleophilic aromatic substitution. In addition to the interesting mechanistic aspect, the present reaction provides a facile synthetic method for a wide range of diaryl ketones, some of which are not easily available through the previously known procedures.