37480-22-1

Upstream product

• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 591-50-4 iodobenzene 
• 75-16-1 methylmagnesium bromide 
• 121-69-7 N,N-dimethyl-aniline 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 91-20-3 naphthalene 
• 90-15-3 α-naphthol 

Relevant academic research and scientific papers

Aminomethylation of Oxabenzonorbornadienes via the Merger of Photoredox and Nickel Catalysis

The first aminomethylation of oxabenzonorbornadienes using dual photoredox/nickel catalysis has been disclosed. This cascade reaction allowed the preparation of the cis-aminomethyl dihydronaphthalenols without any prefunctionalization or any use of nucleophilic organometallic species. The control of the regio-and stereoselectivity might be explained by a sequence involving insertion of nickel(0) into the C-O bond followed by the formation of a π-allyl intermediate.

Nickel-catalyzed highly stereoselective ring opening of 7-oxa- and azanorbornenes with organic halides

Nickel-catalyzed ring-opening reactions of 7-heteroatom norbornadienes and norbornenes with various organic halides to give products with multiple stereocenters are described. Treatment of 7-oxabenzonorbornadiene (1a) and 7- carbomethoxy-7-azabenzonorbornadiene (1b) with aryl iodides (ArI) in the presence of NiCI2(PPh3)2 and Zn powder gave the corresponding ring- opening addition products cis-1,2-dihydro-2-aryl-1-naphthol (2a-m) and methyl N-[cis-1,2-dihydro-2-aryl-1-naphthyl]carbamate (3a-e) completely stereoselectively in 40-99% yields. The nickel system also catalyzes the reaction of highly substituted oxabicyclic [2.2.1] compounds (1c-e) with organic halides (PhI, PhCH2Br, PhCHCHBr, and PhCBrCH2) to give the corresponding ring-opening products (4a-d, 5, 6a,b) that consist of four fixed stereocenters. Studies on the effect of solvent on the reaction of 1a with PhI show that CH3CN gives the highest yield of product 2a; no product 2a is observed when toluene, dichloromethane, methanol, DMF, or DMSO is used as solvent. Addition of extra PPh3 to the reaction mixture reduced the yield of 2a. A mechanism is proposed to account for the formation of these nickel- catalyzed ring-opening addition products.

Copper-catalyzed ring-opening of heterobicyclic alkenes with Grignard reagents: Remarkably high anti-stereocontrol

Unlike most of the reported protocols for the ring-opening reaction of heterobicyclic alkenes with carbon nucleophiles which typically occur with syn selectivity, the alkylative ring-opening reaction of [2.2.1]oxa- and azabicyclic alkenes with Grignard reagents in the presence of a catalytic amount of copper(I) takes place with very high or complete anti-stereocontrol under smooth reaction conditions. This new procedure proved to be wide in scope with respect to both the Grignard reagent and the bicyclic alkene. Especially noteworthy is the facile ring-opening reaction of low reactive substrates such as nonaromatic oxabicyclic alkenes and azabenzonorbornadienes under this catalyst system. Georg Thieme Verlag Stuttgart.

Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with Grignard reagents

(Chemical Equation Presented) Simple Grignard reagents were applied in copper-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadiene derivatives using spiro phosphoramidite ligands. Excellent anti- stereoselectivities and good enantioselecti

Copper-catalyzed anti-stereocontrolled ring opening of oxabicyclic alkenes with Grignard reagents

(Matrix presented) A general copper-catalyzed procedure for the stereoselective ring opening of [2.2.1]-oxabicyclic alkenes with Grignard reagents is described. In the presence of catalytic amounts of CuCl/PPh 3 the reaction occurs with very high or complete anti selectivity in all cases.