1833-48-3Relevant academic research and scientific papers
Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands
Dilauro, Giuseppe,Azzollini, Claudia S.,Vitale, Paola,Salomone, Antonio,Perna, Filippo M.,Capriati, Vito
supporting information, p. 10632 - 10636 (2021/04/09)
Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.
Neutral, cationic and anionic organonickel and -palladium complexes supported by iminophosphine/phosphinoenaminato ligands
Santiago, Tomás G.,Urbaneja, Carmen,álvarez, Eleuterio,ávila, Elena,Palma, Pilar,Cámpora, Juan
, p. 322 - 335 (2020/01/21)
We report a series of organometallic nickel and palladium complexes containing iminophosphine ligands R2PCH2C(Ph) = N-Dipp (Dipp = 2,6-diisopropylphenyl; R = iPr, La; R = Ph, Lb; and R = o-C6H4OMe, Lc), synthesized by ligand exchange or oxidative addition reactions, and we investigate the capacity of such ligands to undergo reversible deprotonation to the corresponding phosphinoenaminato species. In the attempted ligand exchange reaction of the nickel bis(trimethylsilyl)methyl precursor [Ni(CH2SiMe3)2Py2] with Lb, the iminophosphine acts as a weak acid rather than a neutral ligand, cleaving one of the Ni-C bonds, to afford the phosphinoenaminato complex [Ni(CH2SiMe3)(L′b)(Py)] (L′b = conjugate base of Lb). We disclose a general method for the syntheses of complexes [Ni(CH2SiMe3)(L)(Py)]+ (L = La, Lb or Lc), and demonstrate that iminophosphine deprotonation is a general feature and occurs reversibly in the coordination sphere of the metal. By studying proton exchange reactions of the cation [Ni(CH2SiMe3)(Lb)(Py)]+ with bases of different strength we show that the conjugate phosphinoenaminato ligand in [Ni(CH2SiMe3)(L′b)(Py)] is a base with strength comparable to DBU in THF. The acyl group in the functionalized aryl complex [Ni(p-C6H4COCH3)(Br)(La)] does not interfere in the iminophosphine deprotonation with NaH. The latter reaction affords the unusual anionic hydroxide species [Ni(p-C6H4COCH3)(OH)(L′a)]-Na+, which was isolated and fully characterized.
B-alkyl suzuki-miyaura cross-coupling reactions with air-stable potassium alkyltrifluoroborates
Molander, Gary A.,Yun, Chang-Soo,Ribagorda, Maria,Biolatto, Betina
, p. 5534 - 5539 (2007/10/03)
The palladium-catalyzed cross-coupling reaction of substituted potassium alkyltrifluoroborates with aryl halides and aryl triflates proceeds readily with moderate to good yields. The potassium alkyltrifluoroborates 1, 2, and 3a-e were easily synthesized and obtained as air-stable crystalline solids that can be stored for long periods of time. All of the cross-couplings proceed under the same reaction conditions using PdCl2(dppf)·CH2cl2 as catalyst in THF-H2O in the presence of 3 equiv of Cs2CO3 as base.
Friedel-Crafts acetylation and benzoylation of benzylsilanes and xanthenes
Georgakilas, Vasilios,Perdikomatis, Gerasimos P.,Triantafyllou, Anastasios S.,Siskos, Michael G.,Zarkadis, Antonios K.
, p. 2441 - 2447 (2007/10/03)
The synthesis of p-acetyl and p-benzoyl derivatives of various benzylsilanes (p-R1CO-C6H4-CR2R3- SiMe3: R1, R2, R3=Me, H, H; Me, H, Ph; Me, H, Me; Me, Me, M
Ag(I)-promoted Suzuki-Miyaura cross-couplings of n-alkylboronic acids
Zou, Gang,Reddy, Y. Krishna,Falck
, p. 7213 - 7215 (2007/10/03)
Ag(I) salts significantly enhance palladium-catalyzed Suzuki-Miyaura cross-couplings of n-alkylboronic acids with a wide variety of aryl and alkenyl halides/triflates.
Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles
Perez,Sestelo,Sarandeses
, p. 4155 - 4160 (2007/10/03)
The novel metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles is described. Triorganoindium compounds (R3In) containing alkyl, vinyl, aryl, and alkynyl groups are efficiently prepared from the correspond
