59115-43-4Relevant academic research and scientific papers
Resorcin[4]arene-derived mono-, bis- and tetra-imidazolium salts as ligand precursors for Suzuki-Miyaura cross-coupling
El Moll, Hani,Semeril, David,Matt, Dominique,Toupet, Loic,Harrowfield, Jean-Jacques
, p. 372 - 382 (2012)
Eleven resorcinarene cavitands bearing either one, two or four (3-R-1-imidazolylium)-methyl substituents (R = nBu, Ph, Mes, iPr2C6H3) anchored at resorcinolic "ortho" positions have been synthesised f
Cyclodiphosphazane appended with thioether functionality: Synthesis, transition metal chemistry and catalytic application in Suzuki-Miyaura cross-coupling reactions
Balakrishna, Maravanji S.,Suresh,Mague, Joel T.
, p. 259 - 265 (2011)
The coordination chemistry of thioether functionalized cyclodiphosphazane ligand, cis-{tBuNP(OCH2CH2SCH 3)}2 (1) is described. The reactions of 1 with [Pd (COD)Cl2] in 1:1, 1:2 and 2:1 M ra
Palladium-catalysed Suzuki-Miyaura cross-coupling with imidazolylidene ligands substituted by crowded resorcinarenyl and calixarenyl units
?ahin, Neslihan,Semeril, David,Brenner, Eric,Matt, Dominique,Kaya, Cemal,Toupet, Lo?c
, p. 1171 - 1179 (2015)
Two N-heterocyclic carbene (NHC) palladium complexes of formula [PdBr2(NHC)(pyridine)] in which the carbenic ring is anked by sterically crowded cavitand substituents were prepared from appropriate imidazolium salts bearing either two resorcina
Nickel-Catalyzed Direct Cross-Coupling of Aryl Sulfonium Salt with Aryl Bromide
Ma, Na-Na,Ren, Jing-Ao,Liu, Xiang,Chu, Xue-Qiang,Rao, Weidong,Shen, Zhi-Liang
, p. 1953 - 1957 (2022/03/27)
The direct cross-couplings of aryl sulfonium salts with aryl halides could be achieved by using nickel as a reaction catalyst. The reactions proceeded efficiently via C-S bond activation in the presence of magnesium turnings and lithium chloride in THF at ambient temperature to afford the corresponding biaryls in moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions employing preprepared organometallic reagents.
Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki-Miyaura cross-coupling reactions
Holzapfel, Cedric W.,Lamola, Jairus L.,Maumela, Munaka Christopher,Moshapo, Paseka T.
, p. 26883 - 26891 (2021/08/17)
A family of biaryl phosphacyclic ligands derived from phobane and phosphatrioxa-adamantane frameworks is described. The rigid biaryl phosphacycles are efficient for Suzuki-Miyaura cross-coupling of aryl bromides and chlorides. In particular, coupling reactions of the challenging sterically hindered and heterocyclic substrates were viable at room temperature.
Palladium complexes derived from benzoylthiourea ligands: Synthesis, crystal structure, and catalytic application in Suzuki C–C coupling reactions
Solmaz, Ummuhan,Gumus, Ilkay,Yilmaz, Mustafa Kemal,Ince, Simay,Arslan, Hakan
, (2021/07/19)
[PdCl2(HL1-κS)2] and [PdCl2(HL2-κS)2] complexes were formed from neutral monodentate modes of HL1 and HL2 ligands, which are coordinated to the palladium(II) center, r
Designing biaryl phosphacyclic ligands: their characterization and evaluation in palladium-catalyzed Suzuki-Miyaura reactions of aryl bromides and chlorides
Holzapfel, Cedric W.,Lamola, Jairus L.,Maumela, Munaka Christopher,Moshapo, Paseka T.
, (2021/12/22)
Efficient palladium catalyst systems based on the combination of bench stable biaryl phosphacycles and Pd(OAc)2 are described for Suzuki-Miyaura cross-coupling reactions of aryl bromides and chlorides. Notably, the electronically and sterically diametric biaryl phosphacycles allowed facile coupling of sterically hindered and heterocyclic substrates.
Monosubstituted, Anionic Imidazolyl Ligands from N?H NHC Precursors and Their Activity in Pd-Catalyzed Cross-Coupling Reactions
Clark, Kyle J.,Ess, Daniel H.,Jensen, Christopher A.,Kenney, Karissa C.,Larson, Alexandra J. S.,Martinez, Erin E.,Michaelis, David J.,Nazari, S. Hadi,Smith, Stacey J.,Valdivia-Berroeta, Gabriel A.
supporting information, (2020/07/06)
We report that treatment of several 2-diphenylphosphinoimidazoles with Pd(II) salts generates monosubstituted N?H NHC?Pd complexes via insertion into the C?P bond. Removal of the N?H proton in situ leads to anionic (X-type) or imidazolyl-Pd complexes that are highly stable and catalytically active, achieving up to 340,000 turnovers at 1 ppm catalyst loading in Suzuki-Miyaura reactions. DFT-calculated Tolman electronic parameters for the sterically small ligands suggest that these ligands are significantly more donating than traditional NHCs, which provides a rationale for rapid cross-coupling catalysis. Excellent reactivity is also demonstrated in Sonogashira reactions. (Figure presented.).
Suzuki-Miyaura Cross-Coupling of Sulfoxides
Abduhulam, Hayrul,Cao, Changsheng,Chen, Qianwei,Dang, Yanfeng,Li, Chengxi,Shi, Yanhui,Wu, Shufeng,Yan, Shuqin
, p. 8168 - 8176 (2020/09/18)
The utilization of diphenyl sulfoxides as versatile electrophilic coupling partners for the Suzuki-Miyaura reaction via C-S bond cleavage was successfully developed under palladium-N-heterocyclic carbene catalysis. The reactions showed good functional group compatibility, proceeded well under mild conditions, and provided biaryls in yields of up to 96%. A wide range of useful functional groups, such as fluoro, chloro, ether, hydroxyl, amide, cyano, keto, trimethylsilyl (TMS), and ester were tolerated under the reaction conditions; however, the use of phenylboronic anhydride and arylboronic acid pinacol esters generally would lead low yields. Good regioselectivity for the electron-poor phenyl group was achieved when unsymmetrical diphenyl sulfoxides were used. The protocol is applicable at the gram scale even with half the amount of catalyst. Density functional theory calculations were performed to investigate the reaction mechanism, indicating that the reaction occurred through oxidative addition, transmetalation, and reductive elimination to provide the final coupling product.
Transition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants
Gerleve, Carolin,Studer, Armido
supporting information, p. 15468 - 15473 (2020/05/06)
Readily prepared tetraarylborates undergo selective (cross)-coupling through oxidation with Bobbitt's salt to give symmetric and unsymmetric biaryls. The organic oxoammonium salt can be used either as a stoichiometric oxidant or as a catalyst in combination with in situ generated NO2 and molecular oxygen as the terminal oxidant. For selected cases, oxidative coupling is also possible with NO2/O2 without any additional nitroxide-based cocatalyst. Transition-metal-free catalytic oxidative ligand cross-coupling of tetraarylborates is unprecedented and the introduced method provides access to various biaryl and heterobiaryl systems.
