29778-31-2Relevant academic research and scientific papers
Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: Synthesis of unsymmetrical diarylethynes
Chen, Qiang,Fu, Liyan,Nishihara, Yasushi
supporting information, p. 7977 - 7980 (2020/09/09)
Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes is described. This reaction not only effectively inhibits the formation of undesired homocoupled products by avoiding the addition of a base, but also exhibits a wide substrate scope to provide a general access to diverse unsymmetrical diarylethynes.
Synthesis of Trisubstituted Acrylic Acids through Nickel-Catalyzed Carbomagnesiation of Alkynes and Carbon Dioxide Fixation
Hung, Chen-Hsun,Santhoshkumar, Rajagopal,Chang, Yu-Che,Cheng, Chien-Hong
supporting information, p. 6924 - 6928 (2018/11/23)
A nickel-catalyzed synthesis of trisubstituted acrylic acids from alkynes, Grignard reagents, and CO2 is reported. The reaction proceeds through carbomagnesiation of the alkyne with Grignard reagent followed by carboxylation with CO2 under mild reaction conditions in short time. Various unsymmetrical alkynes were transformed into the corresponding acid products in good yields with high stereoselectivity.
Sonogashira cross-coupling reaction catalyzed by N-heterocyclic carbene-Pd(II)-PPh3 complexes under copper free and aerobic conditions
Dehimat, Zineb Imene,Ya?ar, Sedat,Tebbani, Dahmane,?zdemir, ?smail
, p. 325 - 334 (2017/09/29)
NHC-Pd-PPh3 complexes with the bulky benzyladamantyl substited N-heterocyclic carbene (NHC) were synthesized and characterised by NMR, HRMS and micro analyse. These complexes were proceeded to Sonogashira-Hagihara coupling reaction between aryl
Sonogashira cross-coupling reaction catalysed by mixed NHC-Pd-PPh3 complexes under copper free conditions
Touj, Nedra,Ya?ar, Sedat,?zdemir, Nam?k,Hamdi, Naceur,?zdemir, ?smail
, p. 59 - 71 (2018/02/27)
Mixed NHC–Pd–PPh3 complexes with a methoxyethyl-substituted N-heterocyclic carbene (NHC) were synthesised and characterised by NMR, HRMS, elemental analysis and X-ray crystallography for complex 3b. These complexes were applied to Sonogashira c
N-Heterocyclic carbene-Pd(II)-PPh3 complexes as a new highly efficient catalyst system for the Sonogashira cross-coupling reaction: Synthesis, characterization and biological activities
Boubakri,Mansour,Harrath,?zdemir,Ya?ar,Hamdi
, p. 183 - 199 (2018/02/09)
A novel series of N-heterocyclic carbene-phosphine palladium(II) complexes has been synthesized and fully characterized by IR, 1H NMR, 13C NMR, and 31P NMR spectroscopies, and elemental analysis. The new N-heterocyclic car
Palladium-catalyzed deacetonative coupling of aryl propargylic alcohols with aryl chlorides in water
Chang, Feng,Liu, Yanping
supporting information, p. 961 - 967 (2017/05/04)
A highly efficient and green process for palladium-catalyzed deacetonative coupling of aryl propargylic alcohols with aryl chlorides has been developed. The reaction occurs smoothly in neat water with 2 mol% PdCl2 as catalyst, and various synthetically useful functional groups, including ether, aldehyde, ketone, and heterocyclics, are well tolerated. Moreover, the reaction could proceed through a consecutive Sonogashira/deacetonative process using 2-methyl-3-butyn-2-ol and aryl chlorides as coupling partners, affording the symmetric alkynes in good yields.
Synthesis and catalytic applications of palladium N-heterocyclic carbene complexes as efficient pre-catalysts for Suzuki-Miyaura and Sonogashira coupling reactions
Boubakri,Yasar,Dorcet,Roisnel,Bruneau,Hamdi,Ozdemir
, p. 5105 - 5113 (2017/07/11)
A new palladium complex series with N-heterocyclic carbene (NHC), pyridine and phosphine ligands, PdCl2(L)NHC (2a-c)(L = NHC), PdCl2(L1)NHC(3a-c)(L1 = pyridine), PdCl2(L2)NHC(4a-c)(L2 = triphenylphosphine) was synthesised and fully characterized. The catalytic activities of these complexes were screened for the Sonogashira and Suzuki-Miyaura reactions between arylhalides and phenylacetylene, and phenylboronic acid, respectively. The results pointed out that the carbene/phosphine complexes 4a-c exhibited excellent catalytic activities as compared to 2a-c, 3a-c, and the well-known systems for the palladium-catalysed Sonogashira reaction. The reactivity of 4a-c in these preliminary Sonogashira coupling tests seems to be higher than that of previously reported catalytic systems based on Pd(NHC) moieties. These new palladium NHC complexes are among the first reported palladium catalysts that are efficient for catalysing the Sonogashira reaction from arylchloride substrates.
Palladium-catalyzed cross-coupling reactions of triarylbismuthanes with terminal alkynes under aerobic conditions
Matsumura, Mio,Yamada, Mizuki,Tsuji, Toshiyuki,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
, p. 70 - 75 (2015/07/15)
Abstract A simple Pd-catalyzed Sonogashira-type cross-coupling reaction using of triarylbismuthanes is described. The reaction of triarylbismuthanes with terminal alkynes in the presence of 5 mol% of Pd(OAc)2, 6 equiv. AgF and 6 equiv. K3PO4 at room temperature afforded the coupling products in good to excellent yield. The reaction proceeded effectively under aerobic conditions, and all three aryl groups on bismuth could be transferred to the coupling products. The reaction was sensitive to the electronic nature of the triarylbismuthanes: substrates bearing an electron-withdrawing group on the aromatic ring showed higher reactivity than those having an electron-donating group.
A Merrifield resin supported Pd-NHC complex with a spacer(Pd-NHC@SP-PS) for the Sonogashira coupling reaction under copper- and solvent-free conditions
Jadhav, Sanjay N.,Kumbhar, Arjun S.,Mali, Sawanta S.,Hong, Chang Kook,Salunkhe, Rajashri S.
, p. 2333 - 2341 (2015/03/18)
Synthetic applications of a polymer supported air-stable palladium NHC complex with a spacer (catalyst 6, Pd-NHC@SP-PS) and without a spacer (catalyst 7, Pd-NHC@PS) have been studied for the Sonogashira cross-coupling reaction. The catalysts were prepared
Synthesis of 4-sulfonatobenzylphosphines and their application in aqueous-phase palladium-catalyzed cross-coupling
Moore, Jane N.,Laskay, Nicholas M.,Duque, Kevin S.,Kelley, Steven P.,Rogers, Robin D.,Shaughnessy, Kevin H.
supporting information, p. 16 - 24 (2015/02/05)
Aqueous-biphasic catalysis offers the potential for safer and more environmentally sustainable synthetic processes. In addition, hydrophilic supporting ligands allow homogeneous catalysts to be readily separated from organic products and potentially reused. The synthesis of two new water-soluble ligand precursors, di-tert-butyl(4-sulfonatobenzyl)phosphonium and di-1-adamantyl(4-sulfonatobenzyl)phosphonium, are reported. The air-stable, zwitterionic phosphonium salts were prepared by the reaction of dialkylphosphines with ethyl 4-bromomethylbenzenesulfonate, which results in a one-pot alkylation followed by deprotection of the ethyl sulfonate. This methodology provides an operationally simpler route to sulfonated benzylphosphines than electrophilic sulfonation. The new phosphine ligands were applied to aqueous-phase Suzuki and Sonogashira couplings of aryl bromides.
