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Upstream product

• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 
• 871817-14-0 2-(2-chlorophenyl)-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

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.

Platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes

A new platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes was developed, which afforded the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ol products in high yields (up to 97%) with moderate to good enantioselectivities (up to 89% ee) under very mild conditions. The effects of various ligands, catalyst loading, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. The cis configuration of product 2m was confirmed by X-ray diffraction analysis. A potential mechanism for the present catalytic reaction is proposed.

Nickel-catalyzed asymmetric ring opening of oxabenzonorbornadienes with arylboronic acids

A new, versatile, and highly efficient nickel-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of arylboronic acids has been developed, yielding cis-2-aryl-1,2-dihydronaphthalen- 1-ols in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under very mild conditions. The effects of various nickel precursors, chiral bidentate ligands, catalyst loadings, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding cis-ring-opened products based on the X-ray structure of product 4b.

One-pot synthesis of chiral dihydrobenzofuran framework via Rh/Pd catalysis

A one-pot synthesis of the chiral dihydrobenzofuran framework is described. The method utilizes Rh-catalyzed asymmetric ring opening (ARO) and Pd-catalyzed C-O coupling to furnish the product in excellent enantioselectivity without isolation of intermedia