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)
-
Frey,H.M.,Midcalfe,J.
, p. 2529 - 2531 (1970)
-
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins
Zhao, Huaibo,McMillan, Alastair J.,Constantin, Timothée,Mykura, Rory C.,Juliá, Fabio,Leonori, Daniele
supporting information, p. 14806 - 14813 (2021/09/18)
We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.