19800-47-6Relevant academic research and scientific papers
Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki-Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene
Gargaro, Samantha L.,Dunson, Bre'Shon,Sieber, Joshua D.
supporting information, p. 511 - 516 (2020/09/21)
The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this process likely occurs through a rare protonolysis/second transmetalation event rather than by the well-established mechanism requiring the involvement of O 2. The scope of this boronic acid homocoupling reaction was investigated and shown to predominate with electron-deficient arylboronic acids. Finally, a good yield of cross-coupling products could be obtained by employing dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand.
Gold (I) and (III) catalyze Suzuki cross-coupling and homocoupling, respectively
Gonzalez-Arellano,Corma,Iglesias,Sanchez
, p. 497 - 501 (2007/10/03)
Trinuclear triphenylphosphine 1,2Au(I) complexes with the [N,N,O]-tridentate unsymmetrical Schiff bases (1,2) catalyze the Suzuki cross-coupling reaction to afford nonsymmetrical biaryls in good yields, whereas the 1,2Au(III) complexes give only arylboronic homocoupling.
Activation of Reducing Agents. Sodium Hydride Containing Complex Reducing Agents. 32. NiCRAL's as Very Efficient Agents in Promoting Cross-Coupling of Aryl Halides
Lourak, Mouhsine,Vanderesse, Regis,Fort, Yves,Caubere, Paul
, p. 4844 - 4848 (2007/10/02)
Nickel-containing complex reducing agents NiCRA-bpy are shown to be the first nickel reagents able to efficiently perform cross-coupling of aryl halides.The presence of KI in the reaction medium generally improves the procedure.The mechanism and influence of the structures of the substrates are discused.
THE PALLADIUM-CATALYSED CONJUGATE ADDITION TYPE REACTION OF ARYLMERCURY COMPOUNDS WITH α,β-UNSATURATED KETONES IN A TWO-PHASE SYSTEM
Cacchi, S.,Misiti, D.
, p. 2941 - 2946 (2007/10/02)
Pd-catalysed reaction of arylmercury compounds with α,β-enones in an acidic two-phase system provides a mild and selective way to β-aryl ketones.The present conjugate addition type reaction may accomodate a wide variety of functional groups.Thus, aryl units containing electron-donating and electron-withdrawing substituents such as -Me, -Cl, -CHO, -COMe, -COOMe, -COOH, -OH, -OMe, -NHCOMe and NO2 were succesfully transfered to the β C atom of benzalacetone.A number of α,β-enones were also treated with 3-formylphenyl mercury chloride to give the corresponding β-(3-formylphenyl) derivatives.The main limitation seems to arise from steric hindrance in the starting α,β-enonic system.Substituents in the aryl moiety of the organomercury compounds were found to affect the transmetalation steps in the direction expected for a rate determining ?-complex formation.
