24382-97-6Relevant academic research and scientific papers
MeOTf-catalyzed formal [4?+?2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion
Chen, Chao,Xi, Chanjuan,Zhang, Zeyu,Zou, Song
supporting information, (2021/12/30)
MeOTf-catalyzed formal [4 + 2] annulation of styrene oxides with alkynes to afford polysubstituted naphthalenes has been realized, which undergoes sequential electrophilic cyclization/ring expansion. A range of substrates were tolerated in the formation of naphthalene derivatives with high regioselectivity in satisfactory yields. The reaction could also be carried out on gram scale.
Lipids as versatile solvents for chemical synthesis
Bayer, Annette,Gevorgyan, Ashot,Hopmann, Kathrin H.
supporting information, p. 7219 - 7227 (2021/09/28)
Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis. Suzuki-Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings proceed with quantitative yields in a range of vegetable oils, fish oil, butter and waxes used as solvents. Appropriate methodologies for high-throughput screening and sustainable isolation techniques applicable for vegetable oils and related lipids are presented.
C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd–NHC complex
Tang, Huiling,Liu, Mengna,Zhu, Meiqi,Cui, Benqiang,Shi, Yanhui,Cao, Changsheng
, (2021/09/15)
We have developed the Suzuki-Miyaura cross-coupling of aryl ammonium salts via C–N bond activation catalyzed by an easily prepared and bench-stable palladium-N-heterocyclic carbene complex. The reaction proceeded well under mild conditions with phenylboronic acid, pinacol ester or anhydride and provided yields of products up to 97% with good functional group compatibility. The direct arylation of arylamine can be performed by a two-step one-pot process and the protocol can be performed on the gram scale.
Nickel-Catalyzed Amination of Aryl Chlorides with Amides
Li, Jinpeng,Huang, Changyu,Wen, Daheng,Zheng, Qingshu,Tu, Bo,Tu, Tao
supporting information, p. 687 - 691 (2021/01/09)
A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.
Arylation of aryllithiums with: S-arylphenothiazinium ions for biaryl synthesis
Morofuji, Tatsuya,Yoshida, Tatsuki,Tsutsumi, Ryosuke,Yamanaka, Masahiro,Kano, Naokazu
, p. 13995 - 13998 (2020/11/21)
Aryllithiums are one of the most common and important aryl nucleophiles; nevertheless, methods for arylation of aryllithums to produce biaryls have been limited. Herein, we report arylation of aryllithiums with S-arylphenothiazinium ions through selective
Small Phosphine Ligands Enable Selective Oxidative Addition of Ar-O over Ar-Cl Bonds at Nickel(0)
Entz, Emily D.,Hooker, Leidy V.,Neufeldt, Sharon R.,Russell, John E. A.
, p. 15454 - 15463 (2020/10/18)
Current methods for Suzuki-Miyaura couplings of nontriflate phenol derivatives are limited by their intolerance of halides including aryl chlorides. This is because Ni(0) and Pd(0) often undergo oxidative addition of organohalides at a similar or faster rate than most Ar-O bonds. DFT and stoichiometric oxidative addition studies demonstrate that small phosphines, in particular PMe3, are unique in promoting preferential reaction of Ni(0) with aryl tosylates and other C-O bonds in the presence of aryl chlorides. This selectivity was exploited in the first Ni-catalyzed C-O-selective Suzuki-Miyaura coupling of chlorinated phenol derivatives where the oxygen-containing leaving group is not a fluorinated sulfonate such as triflate. Computational studies suggest that the origin of divergent selectivity between PMe3 and other phosphines differs from prior examples of ligand-controlled chemodivergent cross-couplings. PMe3 effects selective reaction at tosylate due to both electronic and steric factors. A close interaction between nickel and a sulfonyl oxygen of tosylate during oxidative addition is critical to the observed selectivity.
Immobilized Pd on Eggshell Membrane: A powerful and recyclable catalyst for Suzuki and Heck cross-coupling reactions in water
Wu, Shang,Jiang, Hongyan,Zhang, Hong,Zhao, Lianbiao,Yuan, Peilin,Zhang, Ying,Su, Qiong,Wang, Yanbin,Wu, Lan,Yang, Quanlu
, (2020/09/09)
A stable heterogeneous palladium catalysts, the waste eggshell membrane (ESM) anchored Pd complex, was synthesized by a simple and green technique. The catalyst obtained can display an outstanding catalytic activity for Suzuki and Heck coupling reactions in water media. The reactions of various aryl halides with aryl boronic acids and terminal alkenes provided the corresponding products in moderate to excellent yields. More importantly, this novel and efficient catalyst with high stability can be easily reused for at least twelve times with no decrease of the catalytic activity, performing an endurable and wide tolerance of the substrates. Facile synthesis, high catalytic activity, and recyclability make these catalysts interesting for further studies.
Visible-Light-Promoted, Catalyst-Free Gomberg-Bachmann Reaction: Synthesis of Biaryls
Lee, Juyoung,Hong, Boseok,Lee, Anna
, p. 9297 - 9306 (2019/08/12)
Biaryls were synthesized via a novel visible-light-promoted Gomberg-Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor-acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.
A highly efficient and recyclable NiCl2(dppp)/PEG-400 system for Suzuki-Miyaura reaction of aryl chlorides with arylboronic acids
Liao, Yang,Yang, Weisen,Wei, Ting,Cai, Mingzhong
supporting information, p. 1134 - 1142 (2019/04/10)
NiCl2(dppp) in PEG-400 is shown to be a highly efficient catalyst for Suzuki-Miyaura coupling of aryl chlorides with arylboronic acids. The reaction could be conducted at 100 °C using K3PO4 as base, yielding a variety of biaryls in good to excellent yields. The isolation of the products was readily performed by extraction with petroleum ether and NiCl2(dppp)/PEG-400 system could be easily recycled and reused up to five times without significant loss of activity. Our system not only avoids the use of easily volatile and toxic dioxane or toluene as a solvent but also solves the basic problem of nickel catalyst reuse.
COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Paragraph 0204-0207, (2019/11/21)
The present invention provides a compound represented by chemical formula and an organic light emitting device comprising the same. The organic light emitting device comprising the compound has excellent electrochemical and thermal stability, thereby having excellent lifespan characteristics.COPYRIGHT KIPO 2020
