14621-04-6Relevant articles and documents
Palladium-catalyzed direct arylation of polyfluoroarenes with organosilicon reagents
Fan, Huixin,Shang, Yaping,Su, Weiping
, p. 3323 - 3327 (2014)
The palladium-catalyzed direct arylation of polyfluoroarenes with organosilicon reagents was achieved by establishing general reaction conditions. This protocol was compatible with a broad range of functional groups and offered the desired products in moderate to good yields. Copyright
Palladium nanocrystals stabilized by cucurbit[6]uril as efficient heterogeneous catalyst for direct C-H functionalization of polyfluoroarenes
Cao, Minna,Wu, Dongshuang,Su, Weiping,Cao, Rong
, p. 62 - 69 (2015)
Palladium nanocrystals (Pd NCs) featuring abundant surface defects are successfully synthesized by using cucurbit[6]uril as a stabilizer. Employing the as-prepared Pd NCs as catalyst, an efficient approach to the direct C-H functionalization of electron-d
The effect of N-heterocyclic carbene ligands in the palladium-catalyzed cross-coupling reaction of K[C6F5BF3] with aryl iodides and aryl bromides
Adonin, Nicolay Yu.,Babushkin, Dmitrii E.,Parmon, Valentin N.,Bardin, Vadim V.,Kostin, Gennadiy A.,Mashukov, Vasiliy I.,Frohn, Hermann-Josef
, p. 5920 - 5924 (2008)
The effect of N-heterocyclic carbene (NHC) ligands on the catalytic activity of in situ generated palladium complexes in the model cross-coupling reaction of K[C6F5BF3] with 4-FC6H4I was studied. Based on the obtained results, a series of pentafluorobiphenyls C6F5C6H4X were prepared from K[C6F5BF3] and XC6H4I or 4-CF3C6H4Br in high yields under aerobic conditions.
Evaluating the electronic properties of ditopic and hetero-ditopic ligands derived from benzimidazole and pyrazole by 13C NMR spectroscopy
Huynh, Han Vinh,Lu, Yuchen,Meng, Qi,Teng, Qiaoqiao,Zhu, Rongmei
, (2020)
Huynh's electronic parameter (HEP) was applied to distinguish the electronic properties of benzimidazole and pyrazole donors in N^N ditopic and N^N′ hetero-ditopic, dinucleating ligands by 13C NMR spectroscopy of their dipalladium complexes bea
Direct palladium-catalyzed desulfitative CC coupling of polyfluoroarenes with arylsulfinate salts: Water-accelerated reactions
Lin, Xiaoxi,You, Yi,Weng, Zhiqiang
, p. 76 - 80 (2014)
A new approach to the synthesis of fluorinated biaryl compounds from easily available starting materials is described. This protocol is based on the direct palladium-catalyzed desulfitative cross-coupling of polyfluoroarenes with various arylsulfinate salts via CH bond activation, accelerated by trace amount of water. The method allows the synthesis of various fluorinated biaryl products in moderate to good yields, and tolerated a variety of functional groups, including alkyl, phenyl, methoxy, fluoro, and chloro groups.
Catalytic intermolecular direct arylation of perfluorobenzenes
Lafrance, Marc,Rowley, Christopher N.,Woo, Tom K.,Fagnou, Keith
, p. 8754 - 8756 (2006)
Penta-, tetra-, tri-, and difluorobenzenes undergo direct arylation with a wide range of arylhalides in high yield. Inverse reactivity is observed compared to the common electrophilic aromatic substitution pathway since electron-deficient, C-H acidic aren
Palladium-Catalyzed Carbon–Fluorine and Carbon–Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes
Chen, Wenyi,Hooper, Thomas N.,Ng, Jamues,White, Andrew J. P.,Crimmin, Mark R.
, p. 12687 - 12691 (2017)
Through serendipitous discovery, a palladium bis(phosphine) complex was identified as a catalyst for the selective transformation of sp2C?F and sp2C?H bonds of fluoroarenes and heteroarenes to sp2C?Al bonds (19 examples, 1
Copper-Catalysed Suzuki-Miyaura Cross-Coupling of Highly Fluorinated Aryl Boronate Esters with Aryl Iodides and Bromides and Fluoroarene?Arene π-Stacking Interactions in the Products
Budiman, Yudha P.,Friedrich, Alexandra,Radius, Udo,Marder, Todd B.
, p. 5387 - 5396 (2019)
A combination of copper iodide and phenanthroline as the ligand is an efficient catalyst for Suzuki-Miyaura cross-coupling of highly fluorinated boronate esters (aryl?Bpin) with aryl iodides and bromides to generate fluorinated biaryls in good to excellent yields. This method represents a nice alternative to traditional cross-coupling methods which require palladium catalysts and stoichiometric amounts of silver oxide. We note that π???π stacking interactions dominate the molecular packing in the partly fluorinated biaryl crystals investigated herein. They are present either between the arene and perfluoroarene, or solely between arenes or perfluoroarenes, respectively.
Bolton,Sandall
, p. 463,465, 467, 468 (1978)
Highly efficient cross-coupling reactions with the perfluoroorganotrifluoroborate salts K [RFBF3] (RF=C6F5, CF2=CF)
Frohn,Adonin,Bardin,Starichenko
, p. 8111 - 8114 (2002)
Potassium pentafluorophenyl- and trifluorovinyltrifluoroborates, both containing electron-poor organo groups, reacted with iodobenzene and p-substituted iodobenzenes in the presence of palladium compounds and stoichiometric amounts of silveroxide to the f
Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds
Do, Hien-Quang,Daugulis, Olafs
, p. 1128 - 1129 (2008)
An efficient, copper-catalyzed method for the arylation, alkenylation, and benzylation of polyfluoroarenes has been developed. Arenes containing two or more fluorine substituents on the aromatic ring can be efficiently functionalized. The best results are
Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles
Finck, Lucie,Oestreich, Martin
, p. 11061 - 11064 (2021/06/12)
A chemoselective C(sp2)?C(sp2) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N’-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (SNAr). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.
Room-temperature Pd/Ag direct arylation enabled by a radical pathway
Luscombe, Christine K.,Mayhugh, Amy L.
supporting information, p. 384 - 390 (2020/03/27)
Direct arylation is an appealing method for preparing π-conjugated materials, avoiding the prefunctionalization required for traditional cross-coupling methods. A major effort in organic electronic materials development is improving the environmental and economic impact of production; direct arylation polymerization (DArP) is an effective method to achieve these goals. Room-temperature polymerization would further improve the cost and energy efficiencies required to prepare these materials. Reported herein is new mechanistic work studying the underlying mechanism of room temperature direct arylation between iodobenzene and indole. Results indicate that room-temperature, Pd/Ag-catalyzed direct arylation systems are radical-mediated. This is in contrast to the commonly proposed two-electron mechanisms for direct arylation and appears to extend to other substrates such as benzo[b]thiophene and pentafluorobenzene.
