57479-11-5Relevant academic research and scientific papers
Enantioselective Synthesis of Biaryl Atropisomers by Pd-Catalyzed C?H Olefination using Chiral Spiro Phosphoric Acid Ligands
Luo, Jun,Zhang, Tao,Wang, Lei,Liao, Gang,Yao, Qi-Jun,Wu, Yong-Jie,Zhan, Bei-Bei,Lan, Yu,Lin, Xu-Feng,Shi, Bing-Feng
supporting information, p. 6708 - 6712 (2019/04/26)
The discovery of proper ligands to simultaneously modulate the reactivity and effectively control the stereoselectivity is a central topic in the field of enantioselective C?H activation. Herein, we reported the synthesis of axially chiral biaryls by Pd-catalyzed atroposelective C?H olefination. A novel chiral spiro phosphoric acid, STRIP, was identified as a superior ligand for this transformation. A broad range of axially chiral quinoline derivatives were synthesized in good yields with excellent enantioselectivities (up to 98 % ee). Density functional theory was used to gain a theoretical understanding of the enantioselectivities in this reaction.
Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations
Thapa, Surendra,Gurung, Santosh K.,Dickie, Diane A.,Giri, Ramesh
supporting information, p. 11620 - 11624 (2016/02/19)
An efficient copper(I)-catalyzed coupling of triaryl and trialkylindium reagents with aryl iodides and bromides is reported. The reaction proceeds at low catalyst loadings (2 mol %) and generally only requires 0.33 equivalents of the triorganoindium reagent with respect to the aryl halide as all three organic nucleophilic moieties of the reagent are transferred to the products through consecutive transmetalations. The reaction tolerates a variety of functional groups and sterically hindered substrates. Furthermore, preliminary mechanistic studies that entailed the synthesis and characterization of potential reaction intermediates offered a glimpse of the elementary steps that constitute the catalytic cycle.
Catalytic asymmetric hydrogenation of quinoline carbocycles: Unusual chemoselectivity in the hydrogenation of quinolines
Kuwano, Ryoichi,Ikeda, Ryuhei,Hirasada, Kazuki
supporting information, p. 7558 - 7561 (2015/05/04)
The reduction of quinolines selectively took place on their carbocyclic rings to give 5,6,7,8-tetrahydroquinolines, when the hydrogenation was conducted in the presence of a Ru(η3-methallyl)2(cod)-PhTRAP catalyst. The chiral ruthenium catalyst converted 8-substituted quinolines into chiral 5,6,7,8-tetrahydroquinolines with up to 91:9 er. This journal is
Synthesis of biaryls via intramolecular free radical ipso-substitution reactions
Ujjainwalla, Feroze,Da Mata, Maria Lucília E.N.,Pennell, Andrew M.K.,Escolano, Carmen,Motherwell, William B.,Vázquez, Santiago
, p. 6701 - 6719 (2015/08/24)
A variety of functionalised biaryls and heterobiaryls are prepared by intramolecular free radical [1,5]-ipso-substitution using sulfonamide and sulfonate derived tethering chains. The overall efficiency of the process is determined by appropriately positioned substituents on the aromatic acceptor ring. The extension of the process to benzylic sulfonates and their corresponding N-methylsulfonamide alternatives as substrates in potential [1,6]-ipso-substitution reactions leads mainly to the alternative [1,7] addition products.
METHOD FOR PRODUCING UNSATURATED ORGANIC COMPOUND
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Page/Page column 12, (2011/04/14)
A method for producing an unsaturated organic compound represented by the formula (3): [in-line-formulae](Y1)m-1—R1—R2—(Y2)n-1??(3)[/in-line-formulae] wherein Y1 represents R2 or X1, and Y2 represents R1 or B(X2)2, which comprises reacting a compound represented by the formula (1): [in-line-formulae]R1(X1)m??(1)[/in-line-formulae] wherein R1 represents an aromatic group or the like, X1 represents a leaving group and m represents 1 or 2, with a compound represented by the formula (2): [in-line-formulae]R2{B(X2)2}n??(2)[/in-line-formulae] wherein R2 represents an aromatic group or the like, X2 represents a hydroxyl group or the like, and n represents 1 or 2, in the presence of(a) a nickel compound selected from a nickel carboxylate, nickel nitrate and a nickel halide,(b) a phosphine compound such as 1,4-bis(dicyclohexylphosphino) butane,(c) an amine selected from a primary amine and a diamine such as N,N,N′,N′-tetramethyl-1,2-ethanediamine, and(d) an inorganic base.
Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts
So, Chau Ming,Lau, Chak Po,Chan, Albert S. C.,Kwong, Fuk Yee
, p. 7731 - 7734 (2008/12/22)
A family of indolyl phosphine ligands was applied to Suzuki-Miyaura cross-coupling of aryl tosylates. Catalyst loading can be reduced to 0.2 mol % for coupling of nonactivated aryl tosylate. A challenging example for room temperature coupling is realized. The scope of this highly active Pd/L2 system can be extended to other boron nucleophiles, including trifluoroborate salts and boronate esters. The ligand structural comparisons toward the reactivity in tosylate couplings are also described.
