426841-80-7

Upstream product

• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 98-80-6 phenylboronic acid 
• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 
• 2996-92-1 phenyl trimethylsiloxane 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Downstream Products

• 426841-92-1 (1R,2S)-2-phenyl-1,2,3,4,-tetrahydronaphthalen-1-ol 

Relevant academic research and scientific papers

Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Organoboronic Acids

(Equation Presented) The first rhodium(I)-catalyzed asymmetric addition of organoboronic acids to oxabicyclic alkenes is reported. This asymmetric ring-opening (ARO) reaction can proceed in high yield under very mild conditions with electronically diverse

Homogeneous Palladium-Catalyzed Selective Reduction of 2,2′-Biphenols Using HCO 2H as Hydrogen Source

An efficient homogeneous palladium-catalyzed selective deoxygenation of 2,2′-biphenols by reduction of aryl triflates with HCO 2H as the hydrogen source is reported. This protocol complements the current method based on heterogeneous Pd/C-catalyzed hydrogenation with hydrogen gas. This process provided the reduction products in good to excellent yields, which could be readily converted to various synthetically useful molecules, especially ligands for catalytic synthesis.

Water-Promoted Palladium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Alkoxysilanes

Water-promoted palladium-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of alkoxysilanes has been developed in a one-pot fashion, yielding cis-1,2-dihydronaphthalen-1-ols in favourable yields (up to 98%) with gratifying enantioselectivities (up to 98% ee) under mild conditions. To the best of our knowledge, it represents the first example in the ring-opening reactions of oxabicyclic alkenes with alkoxysilanes. Furthermore, the cis-1,2-configuration of product was established by X-ray diffraction analysis, and a possible mechanism for the present catalytic ring-opening reaction was also proposed. (Figure presented.).

Synthesis method of chiral compound of hydrogenated naphthalene structure unit

The invention discloses a synthesis method of a chiral compound of a hydrogenated naphthalene structure unit. In a methylbenzene/water solvent system, under the existence of catalysts of palladium acetate and R-(+)-1,1'-dinaphthalene-2,2'-diphenylphosphane, potassium trifluoroborate derivatives and oxa-benzo norbornene react at the room temperature to obtain the chiral compound of the hydrogenatednaphthalene structure unit through synthesis. The method provided by the invention has the advantages that the raw materials are cheap and can be easily obtained; the reaction conditions are mild; the post treatment is simple; the obtained target product yield and ee value are high.

Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

The asymmetric ring opening reactions of bicyclic alkenes with boronic acids were accomplished by using a highly active palladium/zinc co-catalytic system that was suitable for both azabenzonorbornadienes and oxabenzonorbornadienes, which were transformed to the corresponding chiral hydronaphthalene products in high yields (up to 99%) and high optical purities (up to 98% ee). The reaction protocol is general and mild and displays good functional group tolerance.

Chiral Palladacycle Catalysts Generated on a Single-Handed Helical Polymer Skeleton for Asymmetric Arylative Ring Opening of 1,4-Epoxy-1,4-dihydronaphthalene

Post-polymerization C-H activation of poly(quinoxaline-2,3-diyl)-based helically chiral phosphine ligands (PQXphos) with palladium(II) acetate afforded chiral phosphapalladacycles quantitatively. In situ generated palladacycles exhibited enantioselectivities up to 94 % ee in the palladium-catalyzed asymmetric ring-opening arylation of 1,4-epoxy-1,4-dihydronaphthalenes with arylboronic acids. Polymers with a twist: Poly(quinoxaline-2,3-diyl)-based helically chiral phosphine ligands (PQXphos) have been used to generate chiral phosphapalladacycles. The palladacycles resulted in enantioselectivities of up to 94 % ee in the palladium-catalyzed asymmetric ring-opening arylation of 1,4-epoxy-1,4-dihydronaphthalenes with arylboronic acids.

Diastereoselective Friedel-Crafts alkylation of hydronaphthalenes

An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intramolecular Friedel-Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-c

Palladacycle-catalyzed highly efficient kinetic resolution of 1-hydroxy-2-aryl-1,2-dihydronaphthalenes via dehydration reaction

(Chemical Equation Presented) Palladacycles showed their high efficiency in the kinetic resolution of 1-hydroxy-2-aryl-1,2-dihydronaphthalenes via dehydration, providing optically active products in high yields and high ee with an S factor up to 26. The superiority of a benzylic-substituted palladacycle in asymmetric induction was also demonstrated.

Asymmetric ring-opening reaction of oxabicyclic alkenes with aryl boronic acids catalyzed by P-containing palladacycles

(Chemical Equation Presented) The chiral phosphine-containing palladacycle, synthesized easily from H-MOP, showed its high catalytic activity as well as asymmetric induction ability in ring-opening reaction of oxabicyclic alkenes with arylboronic acids, p

Palladium(II) catalyst systems for the addition of boronic acids to bicyclic alkenes: New scope and reactivity

(Matrix presented) The palladium-catalyzed ring-opening addition of arylboronic acids to heterobicyclic alkenes is reported. Excellent yields are obtained for the addition of a wide variety of arylboronic acids to aza- and oxabicyclic alkenes. This methodology is especially useful in the synthesis of 1-amino-2-aryldihydronaphthalene scaffolds, for which rhodium catalysts are currently unreactive or give complex mixtures. Asymmetric versions of these reactions are under development, and preliminary results are reported.