43029-63-6

Upstream product

• 93-04-9 2-Methoxynaphthalene 
• 98-88-4 benzoyl chloride 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 5672-94-6 1-acetyl-2-methoxynaphthalene 
• 158689-13-5 7-methoxy-1-naphthyl phenyl ketone 

Downstream Products

• 28215-42-1 (3-hydroxy-naphthalen-2-yl)-phenyl-methanone 

Relevant academic research and scientific papers

Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives

Chiral 1,5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship between the substitution of the naphthalene starting materials and reactivity/selectivity is determined by several factors which act in concert: (1) the effect of substituents on the oxidation potential of the substrate, (2) the ability of the substrate to participate in a chelated copper complex which depends on (a) the inherent coordinating ability of the 3-substituent and (b) substituent steric interactions that affect chelation between the 2-hydroxyl and 3-substituent, (3) the effect of substituents on dissociation of the product from the copper catalyst.

Acylation of 2-Methoxynaphthalene with Acyl Clorides in the Presence of a Catalytic Amount of Lewis Acids

The regiochemistry of the reaction of 2-methoxynaphthalene 1 with benzoyl chloride 2a using a catalytic amount of Lewis acid is strongly influenced by the identity of the acid catalyst employed as well as by the reaction temperature.By using InCl3, FeCl3, SnCl4 or ZnCl2 and heating at 160 deg C, 2-benzoyl-6-methoxynaphthalene 4a is selectively produced along with 1-benzoyl-7-methoxynaphthalene 5a, while in the case of AlCl3, SbCl5 or TiCl4, 1-benzoyl-2-methoxynaphthalene 3a is the major product. 2-Acyl-6-methoxynaphthalenes 4b-e can be selectively obtained using InCl3 and the corresponding acyl chlorides 2b-e in place of 2a.In the presence of a stoichiometric amount of InCl3, the reaction of 1 with 2a also gives 4a as the predominant product along with 5a even at 50 deg C.This reaction appears to involve isomerisation of 3a to 4a and 5a.