6311-43-9Relevant academic research and scientific papers
Triphenylphosphine chalcogenides as efficient ligands for room temperature palladium(II)-catalyzed Suzuki-Miyaura reaction
Das, Pankaj,Bora, Utpal,Tairai, Archana,Sharma, Chandan
, p. 1479 - 1482 (2010)
A simple catalytic system based on PdCl2 and triphenylphosphine chalcogenides (PPh3X; X = O, S, Se) is found to be highly effective (up to 97% isolated yield) in the room temperature Suzuki-Miyaura reactions. Under the same experimental conditions, triphenylphosphine chalcogenides as ligands show superior activities compared to free triphenylphosphine.
Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects
Antenucci, Achille,Barbero, Margherita,Dughera, Stefano,Ghigo, Giovanni
, (2020/10/20)
Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.
Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides
Barbero, Margherita,Dughera, Stefano
, p. 5758 - 5769 (2018/09/10)
Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.
Excellent Suzuki–Miyaura catalytic activity of a new Pd(II) complex with sulfonamide–Schiff base ligand
Banik, Biplab,Tairai, Archana,Bhattacharyya, Pradip K.,Das, Pankaj
, p. 519 - 523 (2016/07/16)
A new air-stable Pd(II) complex containing a sulfonamide–Schiff base ligand has been synthesized, characterized and investigated as a catalyst for the Suzuki–Miyaura reactions of aryl halides with arylboronic acids. Theoretical calculations (B3LYP) and spectroscopic evidence suggest that the sulfonamide–Schiff base coordinates to the Pd centre through sulfonamide nitrogen (?SO2NH2) rather than imine (?CH?N). The complex shows excellent cross-coupling activity with aryl bromides in water at room temperature and aryl chlorides in isopropanol at 60°C. Copyright
A highly efficient Schiff-base derived palladium catalyst for the Suzuki-Miyaura reactions of aryl chlorides
Shahnaz, Nasifa,Banik, Biplab,Das, Pankaj
, p. 2886 - 2889 (2013/06/05)
A new palladium complex derived from a bidentate Schiff-base ligand showed excellent activity as catalyst for the Suzuki-Miyaura cross-coupling reactions of less reactive aryl chlorides with arylboronic acids. Under an optimized condition, moderate-to-excellent yields of biaryls were obtained with a wide range of substrates at a relatively low loading of catalyst (0.2 mol %).
Palladium(II)-catalyzed coupling of electron-deficient arenes via C-H activation
Zhou, Lihong,Lu, Wenjun
scheme or table, p. 2124 - 2127 (2012/06/01)
Homocoupling and cross-coupling of electron-deficient arenes, including nitrobenzene, (trifluoromethyl)benzene, ethyl benzoate, etc., have been developed to afford biaryls using a catalytic system of Pd(OAc) 2/trifluoroacetic acid (TFA)/O2 or K2S 2O8. The crucial step is to tune the concentrations of arenes and the loading of TFA carefully to enhance the reaction rates and the selectivity of these couplings involving dual C-H activation.
Protodediazoniation of aryldiazonium fluoroborates by dimethylformamide
Markgraf, J. Hodge,Chang, Raymond,Cort, John R.,Durant Jr., Joseph L.,Finkelstein, Manuel,Gross, Andrew W.,Lavyne, Michael H.,Moore, W. Michael,Petersen, Raymond C.,Ross, Sidney D.
, p. 10009 - 10018 (2007/11/02)
The protodrdiazoniation of aryldiazonium fluoroborates can be effected by warm dimethylformamide (DMF). The conversion of 4-nitrobenzenediazonium fluoroborate to nitrobenzene was studied in detail. Products derived from trapping experiments were consistent with a homolytic process. Studies with deuterated DMF established that H atom abstraction occurred from both sites in DMF with a formyl:methyl preference of 3.5:1.0. This mechanism was consistent with bond energies and kinetic isotope effects calculated for the DMF radical cation.
