300-57-2Relevant articles and documents
Ring-opening 1,3-arylboration of arylcyclopropanes mediated by BCl3
Arisawa, Mitsuhiro,Kuboki, Yuichi,Murai, Kenichi
, p. 37797 - 37799 (2020)
Herein, we report a ring-opening 1,3-arylboration of aryl cyclopropanes using BCl3 in the presence of arene nucleophiles. Formal 1,3-oxy arylation and 1,3-amino arylation of the arylcyclopropane via one-pot derivatization of the installed boron group were also achieved.
Boosting catalyst activity in cis -selective semi-reduction of internal alkynes by tailoring the assembly of all-metal aromatic tri-palladium complexes
Monfredini, Anna,Santacroce, Veronica,Deyris, Pierre-Alexandre,Maggi, Raimondo,Bigi, Franca,Maestri, Giovanni,Malacria, Max
, p. 15786 - 15790 (2016)
Highly symmetric [Pd3]+ clusters that present delocalized metal-metal bonds can catalyse the selective semi-reduction of internal alkynes to cis-alkenes. Studies on factors governing the formation of all-metal aromatics enabled the design of an optimised catalytic system that delivers cis-alkenes with almost complete selectivity on a gram scale with very low catalyst loadings (0.03 mol%).
Gold nanoparticles-graphene hybrids as active catalysts for Suzuki reaction
Li, Yang,Fan, Xiaobin,Qi, Junjie,Ji, Junyi,Wang, Shulan,Zhang, Guoliang,Zhang, Fengbao
, p. 1413 - 1418 (2010)
Graphene was successfully modified with gold nanoparticles in a facile route by reducing chloroauric acid in the presence of sodium dodecyl sulfate, which is used as both a surfactant and reducing agent. The gold nanoparticles-graphene hybrids were characterized by high-resolution transmission electron microscopy, atomic force microscopy, X-ray photoelectron spectroscopy, Raman spectroscopy, X-ray diffraction and energy X-ray spectroscopy. We demonstrate for the first time that the gold nanoparticles-graphene hybrids can act as efficient catalysts for the Suzuki reaction in water under aerobic conditions. The catalytic activity of gold nanoparticles-graphene hybrids was influenced by the size of the gold nanoparticles.
Merging Pd0/PdII Redox and PdII/PdII Non-redox Catalytic Cycles for the Allylarylation of Electron-Deficient Alkenes
Semba, Kazuhiko,Ohta, Naoki,Paulus, Fritz,Ohata, Masaki,Nakao, Yoshiaki
, p. 5035 - 5040 (2021)
An allylarylation of electron-deficient alkenes with aryl boronates and allylic carbonates has been developed. This method allows access to a wide variety of carbon skeletons from readily available starting materials. Mechanistic studies indicate that this reaction is enabled by a cooperative catalysis based on merging Pd0/PdII redox and PdII/PdII non-redox catalytic cycles.
Synthesis, Properties, and Catalytic Application of a Triptycene-Type Borate-Phosphine Ligand
Konishi, Shota,Iwai, Tomohiro,Sawamura, Masaya
, p. 1876 - 1883 (2018)
A borate-containing caged triarylphosphine L-X (X = Na or NBu4), featuring a 9-phospha-10-boratriptycene framework, was synthesized and characterized by NMR spectroscopy and X-ray diffraction analysis. The NMR coupling constant of the corresponding phosphine selenide indicated a higher electron-donating property of the borate-phosphine L compared to that of the 9-phospha-10-silatriptycene derivative (Ph-TRIP). The coordination property of L-X to [PdCl(η3-allyl)]2 was dependent on the countercation, giving a neutral Pd complex [PdCl(η3-allyl)(L-NBu4)] from L-NBu4 in CH2Cl2 or a zwitterionic Pd complex [Pd(η3-allyl)(MeCN)(L)] from L-Na in MeCN/CH2Cl2. Utility of L-X as a ligand for metal catalysis was demonstrated in the Pd-catalyzed Suzuki-Miyaura cross-coupling of aryl chlorides.
Vol'pin et al.
, p. 849 (1971)
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Frey,H.M.,Midcalfe,J.
, p. 2529 - 2531 (1970)
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Cobalt-Catalyzed Kumada Coupling Forming Sterically Encumbered C-C Bonds
Brennan, Marshall R.,Darrow, William T.,Fout, Alison R.,Killion, Jack A.,Leahy, Clare A.
, (2021/12/02)
A Co(acac)3/PN precatalyst was developed and optimized for catalytic Kumada coupling of aryl Grignard reagents to sterically encumbered alkyl halides. The substrate scope demonstrates excellent yields for primary alkyl chlorides and bromides, including good performance using neopentyl chloride and neophyl chloride. Secondary alkyl halides were also successfully arylated in good yields, and the presence of β-hydrogen atoms in a substrate did not inhibit product formation. An intermolecular functional group tolerance screen was conducted which indicates that ester and amide functionality are well tolerated by the reaction conditions. Electrophiles containing ester, pyridine, and nitrile functionality were all coupled with 2-mesitylmagnesium bromide in good yields, supporting tolerance screen results. The intermolecular screen also showed that functional groups which are typically reactive with Grignard reagents such as alcohols and terminal alkynes were not well-tolerated by the reaction.
Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes
Geng, Jiao,Hu, Xingbang,Liu, Qiang,Wu, Youting,Yang, Liu,Yao, Chenfei
, p. 3685 - 3690 (2021/05/31)
Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.