38383-51-6Relevant articles and documents
Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent
Su, Mincong,Huang, Xia,Lei, Chuanhu,Jin, Jian
supporting information, p. 354 - 358 (2022/01/15)
A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.
Copper-Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes
Fu, Bin,Li, Xiaohong,Xiong, Tao,Yuan, Xiuping,Zhang, Qian,Zhang, Qiao
, p. 23056 - 23060 (2020/10/19)
A catalytic defluorinative hydroarylation of alkenes with polyfluoroarenes in the presence of dppbz-ligated Cu catalyst and silanes was developed. This method provides a straightforward and alternative avenue to synthetic important polyfluorinated arenes with readily available and bench-stable alkenes as latent nucleophiles, and therefore avoids conventional reliance on stoichiometric quantities of organometallic reagents. This reaction proceeds under very mild conditions and exhibits good functional group compatibility and high level of regioselectivity. The synthetic potential of this method was further demonstrated by a gram-scale synthesis, and an array of experimental studies were also carried out to elaborate the probable mechanism.
Ni: Vs. Pd in Suzuki-Miyaura sp2-sp2 cross-coupling: A head-to-head study in a comparable precatalyst/ligand system
West, Matthew J.,Watson, Allan J. B.
supporting information, p. 5055 - 5059 (2019/06/03)
The Suzuki-Miyaura reaction is a cornerstone method for sp2-sp2 cross-coupling in industry. There has been a concerted effort to enable the use of Ni catalysis as an alternative to Pd in order to mitigate cost and improve sustainability. Despite significant advances, ligand development for Ni-catalyzed Suzuki-Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study we evaluate the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context.
Highly Selective Semihydrogenation of Alkynes to Alkenes by Using an Unsupported Nanoporous Palladium Catalyst: No Leaching of Palladium into the Reaction Mixture
Lu, Ye,Feng, Xiujuan,Takale, Balaram S.,Yamamoto, Yoshinori,Zhang, Wei,Bao, Ming
, p. 8296 - 8303 (2017/12/08)
We report the highly chemoselective and stereoselective semihydrogenation of alkynes to Z-internal and terminal alkenes by using unsupported nanoporous palladium (PdNPore) as a heterogeneous catalyst under mild reaction conditions (room temperature and 1 atm of H2). The semihydrogenation of various terminal/internal and aromatic/aliphatic alkynes afforded the corresponding alkenes in good chemical yields with high selectivities. PdNPore further showed high chemoselectivity toward terminal alkynes in the presence of internal alkynes, which has not yet been achieved using supported palladium nanoparticle catalysts. H-H heterolysis of H2 on the surface of PdNPore was strongly suggested by deuterium labeling experiments. No Pd leached from PdNPore during the reaction, and the catalyst was easily recovered and reused without a loss of activity.
Generation of the CF3 radical from trifluoromethylsulfonium triflate and its trifluoromethylation of styrenes
Zhang, Cheng-Pan,Wang, Zong-Ling,Chen, Qing-Yun,Zhang, Chun-Tao,Gu, Yu-Cheng,Xiao, Ji-Chang
supporting information; experimental part, p. 6632 - 6634 (2011/06/27)
The CF3 radical was generated from the reaction of S-(trifluoromethyl)diphenylsulfonium triflate with Na2S 2O4 or HOCH2SO2Na under suitable conditions without further reduction. Based on this, a method for the synthesis of α-trifluoromethylated ketones has been successfully developed.
Continuous flow palladium(II)-catalyzed oxidative heck reactions with arylboronic acids
Odell, Luke R.,Lindh, Jonas,Gustafsson, Tomas,Larhed, Mats
experimental part, p. 2270 - 2274 (2010/07/10)
Palladium(II)-catalyzed oxidative Heck reactions were investigated under continuous flow conditions. Selective, fast and convenient protocols for the coupling of arylboronic acids with electron-rich and electron-poor olefins were developed by using a commercially available flow reactor.
Synthesis of Styrenes by Palladium(II)-Catalyzed Vinylation of Arylboronic Acids and Aryltrifluoroborates by Using Vinyl Acetate
Lindh, Jonas,Saevmarker, Jonas,Nilsson, Peter,Sjoeberg, Per J. R.,Larhed, Mats
supporting information; experimental part, p. 4630 - 4636 (2009/12/26)
Reactions of aromatic and heteroaromatic boronic acids or aryltrifluoroborate salts with vinyl acetate in the presence of a palladium(II) catalyst give the corresponding styrenes in good yields. This Heck reaction proceeds with microwave heating in less t
Selective functionalization of arenes through the reaction of aryne-zirconocene complexes and enol ethers
Barluenga, José,Fernández, Amadeo,álvarez-Rodrigo, Lucía,Rodríguez, Félix,Fa?anás, Francisco J.
, p. 2513 - 2515 (2007/10/03)
A new method for the selective functionalization of aromatic rings by the zirconium promoted cross coupling reaction of an aryllithium compound and an enol ether is reported. Formation of an aryne-zirconocene complex and its regioselective coupling with a
