53040-92-9Relevant articles and documents
Synthesis and Reactivity of N-Heterocyclic PSiP Pincer Iron and Cobalt Complexes and Catalytic Application of Cobalt Hydride in Kumada Coupling Reactions
Xiong, Zichang,Li, Xiaoyan,Zhang, Shumiao,Shi, Yaomin,Sun, Hongjian
, p. 357 - 363 (2016)
The new N-heterocyclic σ-silyl pincer ligand HSiMe(NCH2PPh2)2C6H4 (1) was designed. A series of tridentate silyl pincer Fe and Co complexes were prepared. Most of them were formed by chelate-assisted Si-H activation. The typical iron hydrido complex FeH(PMe3)2(SiMe(NCH2PPh2)2C6H4) (2) was obtained by Si-H activation of compound 1 with Fe(PMe3)4. The combination of compound 1 with CoMe(PMe3)4 afforded the Co(I) complex Co(PMe3)2(SiMe(NCH2PPh2)2C6H4) (3). The Co(III) complex CoHCl(PMe3)(SiMe(NCH2PPh2)2C6H4) (5) was generated by the reaction of complex 1 with CoCl(PMe3)3 or the combination of complex 3 with HCl. However, when complex 3 was treated with MeI, the Co(II) complex CoI(PMe3)(SiMe(NCH2PPh2)2C6H4) (4), rather than the Co(III) complex, was isolated. The catalytic performance of complex 5 for Kumada coupling reactions was explored. With a catalyst loading of 5 mol %, complex 5 displayed efficient catalytic activity for Kumada cross-coupling reactions of aryl chlorides and aryl bromides with Grignard reagents. This catalytic reaction mechanism is proposed and partially experimentally verified.
Synthesis of novel bisphosphine-containing polymers and their applications as bidentate ligands for nickel(0)-catalyzed cross-coupling reactions
Lu, Yong,Plocher, Elizabeth,Hu, Qiao-Sheng
, p. 841 - 845 (2006)
The efficient synthesis of two examples of a new type of ferrocene-based bisphosphine-containing polymers and their application as bidentate ligands for Ni(0)-catalyzed cross-coupling reactions of aryl chlorides with arylboronic acids, and aryl fluorides with Grignard reagents are described. Our study may provide a new family of bisphosphine-containing polymers that are readily accessible and potentially useful in transition metal catalysis.
Electronic nature of N-heterocyclic carbene ligands: Effect on the Suzuki reaction
Hadei, Niloufar,Kantchev, Eric Assen B.,O'Brien, Christopher J.,Organ, Michael G.
, p. 1991 - 1994 (2005)
(Chemical Equation Presented) Suzuki reactions of aryl chlorides and arylboronic acids with a range of electronically different N-heterocyclic carbene ligands derived from N,N-diadamantylbenzimidazolium salts are reported. Results indicate that an electron-rich NHC ligand enhances the rate of oxidative addition. However, reductive elimination is unchanged by the electronic nature of the supporting ligand and is primarily affected by the steric environment.
Well-dispersed N-heterocyclic carbene–palladium complex anchored onto poly(acrylic acid)/poly(vinyl alcohol) nanofibers: Novel, superior and ecofriendly nanocatalyst for the Suzuki–Miyaura cross-coupling reaction
Heidari, Bahareh,Heravi, Majid M.,Nabid, Mohammad Reza,Sedghi, Roya
, (2019)
Polymeric nanocomposite@Pd is one of the crown jewels for the catalysis of cross-coupling reactions. This Pd nanocomposite on various polymeric supports has been well established to catalyze cross-coupling reactions, but its preparation supported on the surface of nanofibers has been largely overlooked. Herein, we report the preparation of a poly(acrylic acid) (PAA)/poly(vinyl alcohol) (PVA) nanofiber-supported N-heterocyclic carbene–Pd complex. The first step involves the preparation of PAA/PVA nanofibers using the electrospinning process. The second step comprises the reaction of water-soluble poly(ethylene glycol)-imidazole with modified PAA/PVA nanofibers followed by introduction of PdCl2 to achieve successfully the desired nanocomposite. The catalytic activity of this nanocomposite was examined in the expeditious synthesis of biaryl compounds using the Suzuki–Miyaura cross-coupling reaction under mild reaction conditions. The composite offers multiple features such as good hydrophilic properties, high surface area, admirable potential in repeatability tests and being recyclable for several runs without significant loss in its activity under the optimum reaction conditions. Our results showed the superior applicability of this novel nanocatalyst in terms of conversion reaction, yields and turnover frequencies. The structure of the catalyst was characterized using a variety of techniques.
Organozinc pivalate reagents: Segregation, solubility, stabilization, and structural insights
Hernan-Gomez, Alberto,Herd, Emma,Hevia, Eva,Kennedy, Alan R.,Knochel, Paul,Koszinowski, Konrad,Manolikakes, Sophia M.,Mulvey, Robert E.,Schnegelsberg, Christoph
, p. 2706 - 2710 (2014)
The pivalates RZnOPiv×Mg(OPiv)X×n LiCl (OPiv=pivalate; R=aryl; X=Cl, Br, I) stand out amongst salt-supported organometallic reagents, because apart from their effectiveness in Negishi cross-coupling reactions, they show more resistance to attack by moist air than conventional organometallic compounds. Herein a combination of synthesis, coupling applications, X-ray crystallographic studies, NMR (including DOSY) studies, and ESI mass spectrometric studies provide details of these pivalate reagents in their own right. A p-tolyl case system shows that in [D8]THF solution these reagents exist as separated Me(p-C6H4)ZnCl and Mg(OPiv)2 species. Air exposure tests and X-ray crystallographic studies indicate that Mg(OPiv)2 enhances the air stability of aryl zinc species by sequestering H2O contaminants. Coupling reactions of Me(p-C6H4)ZnX (where X=different salts) with 4-bromoanisole highlight the importance of the presence of Mg(OPiv)2. Insight into the role of LiCl in these multicomponent mixtures is provided by the molecular structure of [(THF)2Li2(Cl) 2(OPiv)2Zn]. (un)Mixing cocktails: The secret ingredient in complicated multicomponent organozinc solution mixtures is magnesium pivalate, which enhances the air stability of Zn-C bonds by cleaning up OH - or O2- antagonists and capturing H2O molecules, thus making these contaminants less accessible to carry out hydrolysis.
Cyclopalladated ferrocenylimine functionalized polymer brushes film and its mechanism investigation of heterogeneous catalysis
Fu, Zhihua,Li, Tiesheng,He, Xiaohang,Liu, Jie,Xu, Wenjian,Wu, Yangjie
, p. 293 - 299 (2014)
A highly active, reusable and stable cyclopalladated ferrocenylimine functionalized polymer brushes film (Pd/PBs) had been developed. The Pd/PBs was tested in Suzuki reaction and displayed high activity for the preparation of various biaryls at elevated temperatures in neat water without ligands. Good reusability and stability were presented as that catalytic film could be reused at least eight times with little Pd leaching into the crude product. The reasonable and feasible reaction mechanism of the heterogeneous Suzuki reaction was deeply explored, in which a catalytic cycle of PdII to Pd0 and Pd0 to PdII on the surface was clearly detected and illustrated. In this approach, the coupling reaction catalyzed by active Pd species on the surface of nano-films had proceeded via a mechanism of surface-catalyzed process.
Pd Nanoparticles Immobilized on Supported Magnetic GO@PAMPS as an Auspicious Catalyst for Suzuki–Miyaura Coupling Reaction
Asadi, Shima,Sedghi, Roya,Heravi, Majid M.
, p. 2045 - 2056 (2017)
A novel catalytic system based on palladium nanoparticles (Pd-NPs) immobilized onto the surface of graphene oxide (GO) modified by poly 2-acrylamido-2-methyl-1-propansulfonic acid decorated with magnetic Fe3O4 was designed, prepared and fully characterized. It was successfully examined as a highly efficient heterogeneous catalyst in the Suzuki–Miyaura cross coupling reaction. The results showed excellent catalytic activity for the cross coupling of aryl bromides, alkyl iodides as well as aryl chlorides as the challenging substrates. It was easily separated by an external magnet and reused without any pre-activation at least in seven consecutive runs without any loss in its catalytic activity as well as any detectable Pd leaching. This study demonstrates the great potential of polymeric-functionalized GO as a support owing to its high loading and suitable dispersing of Pd-NPs, for the development of metal–graphene nanocomposites in industrial scale. Graphical Abstract: [Figure not available: see fulltext.].
Amido pincer complex of nickel-catalysed Kumada cross-coupling reactions
Wang, Zhong-Xia,Wang, Li
, p. 2423 - 2425 (2007)
Novel nickel complexes bearing P,N,P-, P,N,N- and N,N,N- amido pincer ligands exhibited highly catalytic activity in Kumada coupling reactions. The Royal Society of Chemistry.
Palladium-Imidazol-2-ylidene Complexes as Catalysts for Facile and Efficient Suzuki Cross-Coupling Reactions of Aryl Chlorides with Arylboronic Acids
Zhang, Chunming,Huang, Jinkun,Trudell, Mark L.,Nolan, Steven P.
, p. 3804 - 3805 (1999)
-
Triphenylphosphine as a ligand for room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl chlorides with arylboronic acids
Tang, Zhen-Yu,Hu, Qiao-Sheng
, p. 2167 - 2169 (2006)
Room-temperature Ni(0)-catalyzed cross-coupling reactions of deactivated aryl chlorides with arylboronic acids with inexpensive triphenylphosphine (PPh3) as a supporting ligand have been accomplished in good to excellent yields. Air-stable Ni(PPh3)2Cl2 has also been established as catalyst precursor, and highly active nickel catalysts were obtained when the reduction of Ni(PPh3)2Cl 2 with n-BuLi was carried out in the presence of an aryl chloride.
A highly active and stable imidazolidine-bridged N,O-donor ligand for efficient palladium catalyzed Suzuki-Miyaura reactions in water
Xue, Jun,Zhou, Zhonggao,Liu, Yulan,Huang, Li,Yu, Hongwei,Xie, Yongrong,Lai, Chen
, p. 331 - 335 (2012)
We have used the sterically hindered N,O-donor ligand 1,4-bis(2-hydroxy-3, 5-di-tert-butyl-benzyl)-imidazolidine with various Pd salts as a catalyst for the Suzuki reaction. This system exhibited excellent catalytic activity in Suzuki reactions of arylboronic acids with aryl halides, including aryl iodides, aryl bromides and activated aryl chlorides, using aqueous methanol as solvent under mild conditions. The catalytic system can be reused once without significant loss of activity. Graphical Abstract: The sterically hindered imidazolidine-bridged mixed nitrogen, oxygen ligand 1 was efficient for Pd-catalyzed Suzuki reactions involving aryl iodides, aryl bromides and activated aryl chlorides with arylboronic acid in aqueous methanol with K 2CO3 as a base the high catalytic activity and oxygen or moisture stable of palladium complexes maybe distribute to the bulky tert-butyl effect.[Figure not available: see fulltext.]
Synthesis and characterization of palladium nanoparticles immobilized on graphene oxide functionalized with triethylenetetramine or 2,6-diaminopyridine and application for the Suzuki cross-coupling reaction
Mirza-Aghayan, Maryam,Mohammadi, Marzieh,Boukherroub, Rabah
, (2021/11/22)
Graphene oxide (GO) was functionalized with two organic ligands, triethylenetetramine (TETA) or 2,6-diaminopyridine (DAP), followed by palladium nanoparticles (Pd NPs) for the synthesis of Pd NPs/GO-TETA and Pd NPs/GO-DAP nanocomposites, respectively. The two heterogeneous nanocomposites were fully characterized and their efficiency was investigated for C[sbnd]C bond formation for the synthesis of biaryl compounds via the Suzuki cross-coupling reaction of aryl halides with arylboronic acid derivatives. The obtained results indicated that the Pd NPs/GO-TETA nanocomposite was more effective in the Suzuki coupling reaction as compared to Pd NPs/GO-DAP. Thus, the Suzuki cross-coupling reaction of different aryl halides with arylboronic acid derivatives using Pd NPs/GO-TETA nanocomposite catalyst in the presence of Na2CO3 as base in DMF/H2O (1/1) as solvent at 90 °C was carried out to afford the desired biaryl compounds in high to excellent yields (81–100%) and short reaction times (10–90 min). Additionally, Pd NPs/GO-TETA nanocomposite can be recovered and reused for 8 consecutive runs without any apparent loss of its catalytic activity, proving its high stability and potential use in organic transformations.
Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes
Ghaderi, Arash,Kambe, Nobuaki,Le, Liyuan,Lu, Hao,Qiu, Renhua,Tang, Ting,Tong, Zhou,Wong, Wai-Yeung,Xu, Zhi,Yin, Shuang-Feng,Zeng, Dishu,Zhang, Dejiang,Zhang, Zhao
, p. 854 - 867 (2022/01/19)
Herein, we disclose a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines by the nickel-catalyzed cross-coupling of halostibines with organic halides. The synthesized Sb-aryl stibines couple with aryl halides to give biaryls efficiently via palladium catalysis. Sequential reactions of stibines with polyhalogenated arenes bearing active C–I/C–Br sites and inactive C–Cl sites successfully proceeded, resulting in the formation of a variety of complex molecules with good site selectivity. Drugs such as diflunisal and fenbufen, as well as a fenofibrate derivative, were synthesized on gram scales in good yields, together with the high recovery of chlorostibine. Furthermore, catalytic mechanisms are proposed based on the results of control experiments.
