3172-56-3Relevant articles and documents
AN EFFICIENT ROUTE TO HETEROARENE-SUBSTITUTED VINYL- AND ALLYL-SILANES VIA PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING
Minato, Akio,Suzuki, Keizo
, p. 83 - 86 (1984)
Heteroarene-substituted vinyl- and allyl-silanes were obtained in good yields by the cross-coupling reaction of either heteroaryl Grignard reagents with halovinyl- and haloallyl-silanes or, alternatively, silyl- and silylmethyl-substituted vinylmetallic reagents with heteroaryl halides in the presence of PdCl2(dppb) as a catalyst.
Synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines
Verbitskiy,Cheprakova,Pervova,Danagulyan,Rusinov,Chupakhin,Charushin
, p. 689 - 694 (2015)
An efficient method for the synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines by the ring transformation in the corresponding pyrimidines was developed. Further modification of the pyridines obtained under conditions of a room temperature aerobic Suzuki reaction in the presence of trans-bis(dicyclohexylamine)palladium(II) acetate as a catalyst was studied
Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
supporting information, p. 1929 - 1940 (2022/02/01)
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
Photoelectric properties of aromatic triangular tri-palladium complexes and their catalytic applications in the Suzuki-Miyaura coupling reaction
Li, Jia,Li, Xujun,Liu, Xiang,Maestri, Giovanni,Malacria, Max,Wang, Xiaoshuang,Wang, Yanlan,Wu, Lingang
supporting information, p. 11834 - 11842 (2021/09/06)
The photoelectric properties and catalytic activities of substituted triphenylphosphine and sulfur/selenium ligand supported aromatic triangular tri-palladium complexes1-4, abbreviated as [Pd3]+, were investigated. The cyclic voltammogram of [Pd3]+in CH3CN-nBu4NPF6showed a single quasi-reversible wave which was consistent with their robust property and provided preliminary proof for their electron transfer processes in catalysis. With excitation at 267 nm, [Pd3]+exhibited strong ratiometric fluorescence at 550 and 780 nm at a temperature gradient from 77 K to 287 K. These peculiar triangular tri-palladium complexes showed excellent catalytic activities and exclusive reactivity with aryl iodides over the other halogenated aromatics in the Suzuki-Miyaura coupling reaction. The electronic and steric hindrance effects of substituents on the aryl iodides and aryl boronic acids including heteroaromatics like pyridine, pyrazine and thiophenes were explored and most substrates achieved up to 99% of yields. (2-[1,1′-Biphenyl]-2-ylbenzothiazole) which was analogous to the selective cyclooxygenase-2 (COX-2) inhibitors was also synthesized with our tri-palladium catalyst and gave good isolated yield (94%). The study of the catalytic process revealed that the mechanism of the reaction may involve the replacement of the sulphur ligand on [Pd3]+by iodine from aryl iodides, which was beneficial for the matching of C-I bond energy.
"benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers
Minus, Matthew B.,Moor, Sarah R.,Pary, Fathima F.,Nirmani,Chwatko, Malgorzata,Okeke, Brandon,Singleton, Josh E.,Nelson, Toby L.,Lynd, Nathaniel A.,Anslyn, Eric V.
supporting information, p. 2873 - 2877 (2021/05/05)
Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.
Three-dimensional covalent organic frameworks based on a π-conjugated tetrahedral node
Gu, Zhangjie,Shan, Zhen,Wang, Jinjian,Wu, Miaomiao,Wu, Xiaowei,Xu, Bingqing,Zhang, Gen
supporting information, p. 10379 - 10382 (2021/10/12)
The construction of three-dimensional (3D) covalent organic frameworks (COFs), especially fully conjugated 3D COFs, is a long-standing challenge. Herein, we report a saddle-like, π-conjugated cyclooctatetrathiophene (COTh) as a tetrahedral node to construct fully conjugated 3D COFs. The present work enriches the structural diversities and potential applications of 3D COFs.
Green-Synthesized Nickel Nanoparticles on Reduced Graphene Oxide as an Active and Selective Catalyst for Suzuki and Glaser-Hay Coupling Reactions
Murugan, Karthik,Nainamalai, Devarajan,Kanagaraj, Pavithara,Nagappan, Saravana Ganesan,Palaniswamy, Suresh
, (2020/07/09)
A mild and benign methodology to syntheses biaryls and 1,3-diynes has been demonstrated using the nickel nanoparticles supported on reduced graphene oxide (RGO-Ni) as a heterogeneous catalyst which is prepared using green reagents. A series of substituted biaryls and 1,3-diynes has been synthesised in good to excellent yields through C-C homocoupling reaction of arylboronic acids and terminal alkynes respectively using 1,4-dioxane as a benign solvent. The present ligand-free catalytic system proceeds smoothly under mild conditions, avoids noble and stoichiometric metal reagents and tolerates sensitive functional groups. Also has a wide substrate scope and feasible with other nitrogen and sulphur containing heteroaryl boronic acids. Hot filtration test unambiguously proves the true heterogeneity of the catalyst and which support for the further reusability of the catalyst for several times without any change in the activity. The easy preparation and simple magnetic separation, stability and reusability reveal that as-prepared RGO-Ni as a versatile catalyst for the synthesis of polyaromatic compounds both in academia and industries. Highlights: Green-synthesized RGO-Ni nanocomposite used as a heterogeneous catalyst for Suzuki type (C-C) and Glaser–Hay (C ≡ C) homocoupling coupling reactions. Ligand-free catalytic system and avoids noble and stoichiometric metal reagents Short reaction time with a minimum catalyst (nickel) loading RGO-Ni nanocomposite is highly stable, reusable, and magnetically retrievable.
Synthesis of Sulfur-Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction
Liu, Shuli,Huang, Chengting,Zhang, Jing,Tian, Siyu,Li, Chang,Fu, Nina,Wang, Lianhui,Zhao, Baomin,Huang, Wei
, p. 3061 - 3070 (2019/05/22)
We present herein a strategy towards the straightforward synthesis of a novel sulfur-hybridized pyracylene, tetraceno[5,6-bc:11,12-b'c']dithiophene (TDT) derivatives, via 2-fold FeCl3-mediated Scholl reaction. Surprisingly, the substituents on the precursors will guide the synthetic route, when the substituents were bromo- or phenyl-, quantitatively debromination or phenyl ring shift mediated rearrangement were observed respectively, the rearrangement products were identified by the HR-Mass and 2D NMR analyses. Additionally, a retrosynthetic method was adopted to confirm the unexpected reaction results in rearrangement of Scholl reaction.
Self-assembly of catalytically active supramolecular coordination compounds within metal?organic frameworks
Adam, Rosa,Mon, Marta,Greco, Rossella,Kalinke, Lucas H.G.,Vidal-Moya, Alejandro,Fernandez, Antonio,Winpenny, Richard E.P.,Domenech-Carbo, Antonio,Leyva-Perez, Antonio,Armentano, Donatella,Pardo, Emilio,Ferrando-Soria, Jesus
supporting information, p. 10350 - 10360 (2019/08/20)
Supramolecular coordination compounds (SCCs) represent the power of coordination chemistry methodologies to self-assemble discrete architectures with targeted properties. SCCs are generally synthesized in solution, with isolated fully coordinated metal atoms as structural nodes, thus severely limited as metal-based catalysts. Metal?organic frameworks (MOFs) show unique features to act as chemical nanoreactors for the in situ synthesis and stabilization of otherwise not accessible functional species. Here, we present the self-assembly of PdII SCCs within the confined space of a pre-formed MOF (SCCs@MOF) and its post-assembly metalation to give a PdII?AuIII supramolecular assembly, crystallography underpinned. These SCCs@MOFs catalyze the coupling of boronic acids and/or alkynes, representative multi-site metal-catalyzed reactions in which traditional SCCs tend to decompose, and retain their structural integrity as a consequence of the synergetic hybridization between SCCs and MOFs. These results open new avenues in both the synthesis of novel SCCs and their use in heterogeneous metal-based supramolecular catalysis.
Self-Assembly of Catalytically Active Supramolecular Coordination Compounds within Metal-Organic Frameworks
Adam, Rosa,Mon, Marta,Greco, Rossella,Kalinke, Lucas H. G.,Vidal-Moya, Alejandro,Fernandez, Antonio,Winpenny, Richard E. P.,Doménech-Carbó, Antonio,Leyva-Pérez, Antonio,Armentano, Donatella,Pardo, Emilio,Ferrando-Soria, Jesús
supporting information, p. 10350 - 10360 (2019/08/27)
Supramolecular coordination compounds (SCCs) represent the power of coordination chemistry methodologies to self-assemble discrete architectures with targeted properties. SCCs are generally synthesized in solution, with isolated fully coordinated metal atoms as structural nodes, thus severely limited as metal-based catalysts. Metal-organic frameworks (MOFs) show unique features to act as chemical nanoreactors for the in situ synthesis and stabilization of otherwise not accessible functional species. Here, we present the self-assembly of PdII SCCs within the confined space of a pre-formed MOF (SCCs?MOF) and its post-assembly metalation to give a PdII-AuIII supramolecular assembly, crystallography underpinned. These SCCs?MOFs catalyze the coupling of boronic acids and/or alkynes, representative multi-site metal-catalyzed reactions in which traditional SCCs tend to decompose, and retain their structural integrity as a consequence of the synergetic hybridization between SCCs and MOFs. These results open new avenues in both the synthesis of novel SCCs and their use in heterogeneous metal-based supramolecular catalysis.
