149341-34-4Relevant academic research and scientific papers
Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands
Biswas, Aniruddha,Pan, Subarna,Samanta, Rajarshi
, p. 1631 - 1636 (2022/03/14)
An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.
1-aryl isoquinoline compound and synthetic method thereof
-
, (2020/11/25)
The invention belongs to the field of organic synthesis, and discloses a 1-aryl isoquinoline compound, which has a structure shown as a general formula I. In the formula I, R1 and R2 are independentlyselected from hydrogen, alkyl, alkoxy, phenyl, halogen,
Synthesis of IAN-type N,N-Ligands via Dynamic Kinetic Asymmetric Buchwald-Hartwig Amination
Ramírez-López, Pedro,Ros, Abel,Romero-Arenas, Antonio,Iglesias-Sigüenza, Javier,Fernández, Rosario,Lassaletta, José M.
supporting information, p. 12053 - 12056 (2016/10/09)
The Pd0-catalyzed coupling of racemic heterobiaryl bromides, triflates, or nonaflates with aryl/alkyl primary amines using QUINAP as the ligand provides the corresponding axially chiral heterobiaryl amines with excellent yields and enantioselectivities. Reactivity and structural studies of neutral and cationic oxidative addition intermediates support a dynamic kinetic asymmetric amination mechanism based on the labilization of the stereogenic axis in the latter and suggest that coordination of the amine to the Pd center is the stereodetermining step.
Asymmetric synthesis of QUINAP via dynamic kinetic resolution
Bhat, Vikram,Wang, Su,Stoltz, Brian M.,Virgil, Scott C.
, p. 16829 - 16832 (2013/12/04)
A palladium-catalyzed, atroposelective C-P coupling process has been developed for the asymmetric synthesis of QUINAP and its derivatives in high enantiomeric excess. Bromide, triflate (OTf) and 4- methanesulfonylbenzenesulfonate (OSs) precursors were stu
Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation
Allan, Kevin M.,Hong, Boram D.,Stoltz, Brian M.
supporting information; experimental part, p. 4960 - 4964 (2010/02/15)
A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.
Practical preparation and resolution of 1-(2′-diphenylphosphino-1′-naphthyl)isoquinoline: A useful ligand for catalytic asymmetric synthesis
Lim, Chung Woo,Tissot, Olivier,Mattison, Andrew,Hooper, Mark W.,Brown, John M.,Cowley, Andrew R.,Hulmes, David I.,Blacker, A. John
, p. 379 - 384 (2013/09/06)
A practical synthesis of the atropisomerically chiral ligand QUINAP is described, followed by its efficient resolution into enantiomers by employing a deficiency of the chloropalladium complex derived from 1′-(R)-1′-(dimethylamino)-1-ethylnaphthalene. The X-ray structure of the ligand, which crystallises as a conglomerate, is reported.
Chelating retardation effect in nickel assisted phosphinatioa: Syntheses of atropisomeric P,N ligands
Kwong, Fuk Yee,Chan, Albert S.C.,Chan, Kin Shing
, p. 8893 - 8899 (2007/10/03)
Ni(PPh3)2Cl2 was found to be an effective reagent in nickel assisted phosphination of biaryl O,N triflates with chlorodiphenylphosphine to yield atropisomeric P,N ligands. The chelating effect of the substrates in the reaction played an important role. Only the monodentate PPh3 rather than bidentate dppe (1,2-bis(diphenylphosphino)ethane) nickel complex was found to be an effective reagent. (C) 2000 Elsevier Science Ltd.
Synthesis and Resolution of 1-(2-Diphenylphosphino-1-naphthyl)isoquinoline; a P-N Chelating Ligand for Asymmetric Catalysis
Alcock, Nathaniel W.,Brown, John M.,Hulmes, David I.
, p. 743 - 756 (2007/10/02)
A multistep synthesis resulting in a good yield of the title compound has been developed based on the Pd-catalysed coupling of 1-chloroisoquinoline and 2-methoxy-1-naphthylboronic acid (5).The product is converted into the corresponding trifluoromethanesu
