2876-70-2

Usage

InChI:InChI=1/C14H14O2/c1-2-16-14(15)10-11-7-8-12-5-3-4-6-13(12)9-11/h3-9H,2,10H2,1H3

Upstream product

• 1221966-64-8 ethyl 2-azido-2-(naphthalene-2-yl)acetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 91-20-3 naphthalene 

Downstream Products

• 68135-51-3 Ethyl-α-(2-naphthyl)-4b-(2'-isobutyl-4'-methylphenyl)-glutarate 
• 94146-69-7 diethyl α-(2-naphthyl)-β-(4-methoxyphenyl)glutarate 
• 94146-68-6 diethyl α-(2-naphthyl)-β-(3-methoxyphenyl)glutarate 
• 94146-67-5 diethyl α-(2-naphthyl)-β-(2-methoxyphenyl)glutarate 
• 94146-70-0 diethyl α-(2-naphthyl)-β-(3,4-dimethoxyphenyl)glutarate 
• 24743-38-2 2--3-phenyl-glutarsaeure-diaethylester 
• 153876-06-3 2-(2,6-difluorophenyl)-4,5-dihydro-4-(2-naphthalenyl)-oxazole 
• 1391911-26-4 C₁₉H₁₉NO₂S 

Relevant academic research and scientific papers

Iron and manganese catalysts for the selective functionalization of arene C(sp2)-H bonds by carbene insertion

The first examples of the direct functionalization of non-activated aryl sp2 C-H bonds with ethyl diazoacetate (N2CHCO2Et) catalyzed by Mn- or Fe-based complexes in a completely selective manner are reported, with no formation of the frequently observed cycloheptatriene derivatives through competing Buchner reaction. The best catalysts are FeII or MnII complexes bearing the tetradentate pytacn ligand (pytacn= 1-(2-pyridylmethyl)-4,7-dimethyl-1,4,7-triazacyclononane). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remained unmodified, thus the reaction being also selective toward functionalization of sp2 C-H bonds. Exclusive catalysis: Iron- and-manganese-based catalysts selectively functionalize the C(sp2)-H bonds of benzene or alkylbenzenes through the formal insertion of the CHCO2Et group from N2CHCO2Et (see scheme). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remain unmodified.

Gold-catalyzed naphthalene functionalization

The complexes IPrMCl (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene, M = Cu, 1a; M = Au, 1b), in the presence of one equiv of NaBAr'4 (Ar' = 3,5-bis(trifluoromethyl)phenyl), catalyze the transfer of carbene groups: C(R)CO2Et (R = H, Me) from N2C(R)CO2Et to afford products that depend on the nature of the metal center. The copper-based catalyst yields exclusively a cycloheptatriene derivative from the Buchner reaction, whereas the gold analog affords a mixture of products derived either from the formal insertion of the carbene unit into the aromatic C-H bond or from its addition to a double bond. In addition, no byproducts derived from carbene coupling were observed.

Generation of iminyl copper species from α-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere

Figure presented A copper-catalyzed reaction of α-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C-C bond cleavage of a transient iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from α-azidocarbonyl compounds and their C-C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O2 was found to be incorporated into the β-carbon fragment as a carboxylic acid.