16605-99-5Relevant articles and documents
Formation of cine-substitution products in the Suzuki-Miyaura cross-coupling reaction catalyzed by dinuclear palladium complexes
Tsukada, Naofumi,Abe, Tsubasa,Inoue, Yoshio
, p. 1093 - 1102 (2013)
The Suzuki-Miyaura coupling reaction catalyzed by dinuclear palladium complexes gave cine-substitution products along with ordinary ipso-substitution products. In the reaction in (D6)benzene, the ipso position of the cine-substitution product was highly deuterated. The H/D exchange also occurred in various positions of benzene rings. Copyright
Diaminophosphine oxides as preligands for Ni-catalyzed Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids
Hu, Feng,Kumpati, Blessy N.,Lei, Xiangyang
, p. 7215 - 7218 (2014)
The first investigation of air- and moisture-stable diaminophosphine oxides as preligands in the Ni-catalyzed Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids has been reported. The results show that under the optimized reaction conditions, the new catalytic system with a Ni(II) σ-aryl complex as precatalyst and a diaminophosphine oxide as preligand tolerates a variety of functional groups and is efficient for both electron-rich and electron-deficient aryl chlorides, though it shows higher efficiency for activated arylboronic acids than deactivated ones. Steric effects were observed for both aryl chlorides and arylboronic acids.
Suzuki-Miyaura cross-coupling of aryl chlorides in water using ligandless palladium on activated carbon
Lysén, Morten,K?hler, Klaus
, p. 1671 - 1674 (2005)
Aqueous reaction conditions that activate various aryl chlorides in Suzuki-Miyaura cross-coupling have been developed. These environment friendly conditions utilize ligandless Pd/C (Pd concentrations 0.2-2 mol%) that allow easy separation of the catalyst at the end of the reaction. Georg Thieme Verlag Stuttgart.
Biaryl synthesis via suzuki coupling on a solid support
Frenette, Richard,Friesen, Richard W.
, p. 9177 - 9180 (1994)
Aryl boronic acids undergo a facile and efficient palladium catalyzed cross-coupling reaction with aryl bromides and iodides that are bound to a Merrifield resin. Simple transesterification releases the biaryl products from the solid support in excellent purity and yield
Suzuki-Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor
Palencia, Hector,Garcia-Jimenez, Federico,Takacs, James M.
, p. 3849 - 3853 (2004)
A simple N-acylimidazolium salt precursor to a NHC-complexed palladacyclic ligand gives high turnover numbers (107) for Suzuki-Miyaura coupling and is applied to the preparation of biaryls used in the synthesis of coumarins. The results suggest that N-acyl-NHC derivatives can contribute to further expanding the rich chemistry of NHCs.
A synthesis of biaryls via nickel(0)-catalyzed cross-coupling reaction of chloroarenes with phenylboronic acids
Saito, Syun,Sakai, Masaaki,Miyaura, Norio
, p. 2993 - 2996 (1996)
The cross-coupling reaction of phenylboronic acid with chloroarenes to give biaryls was carried out in high yields at 80°C in the presence of the nickel(0) catalyst and K3PO4 (3 equivs) in dioxane. The nickel(0) catalyst prepared in situ from NiCl2(dppf) (10 mol%) and four equivalents of BuLi was recognized to be most effective. The reaction can be applicable for a wide range of chloroarenes having an electron-withdrawing or an electron-donating group such as 4-CN, 4-CHO, 2- or 4-CO2Me, 4-COMe, 4-NHAc, 3- or 4-Me, and 3- or 4-OMe, and 4-NH2.
Polyfluorenes without monoalkylfluorene defects
Sung, Yong Cho,Grimsdale, Andrew C.,Jones, David J.,Watkins, Scott E.,Holmes, Andrew B.
, p. 11910 - 11911 (2007)
A synthetic route to 9,9-dioctyl-9H-fluorene (free of monoalkyl-substituted fluorene defects) by alkylative cyclization of 9-biphen-2-ylheptadecan-9-ol is described. Polyfluorenes prepared by Yamamoto and Suzuki polymerization of the defect-free monomers, when incorporated in light-emitting devices, exhibited minimal green emission attributable to fluorenone formation. By contrast, devices fabricated with polyfluorene arising from conventionally synthesized 9,9-dioctyl-9H-fluorene showed significant emission at 533 nm, even at the turn-on voltage. Incorporation of as little as 0.06 mol % of 9-octyl-9H-fluorene comonomer in polyfluorene led to evolution of green fluorescence in the photoluminescence (PL) and electroluminescence (EL) emission spectra. Copyright
Palladium on activated carbon - A recyclable catalyst for Suzuki-Miyaura cross-coupling of aryl chlorides in water
Lysen, Morten,Koehler, Klaus
, p. 692 - 698 (2006)
Aryl chlorides are efficiently coupled with aryl boronic acids using ligandless Pd/C in water. The catalyst is easily recovered via filtration and reused up to four times with an overall yield of 73%. In addition the catalytic activity and selectivity of a variety of homogeneous and heterogeneous palladium sources have been compared. Georg Thieme Verlag Stuttgart.
'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction
Ding, Chengrong,Guan, Chenfei,Miao, Huihui,Zhang, Guofu,Zhao, Yiyong
supporting information, p. 3560 - 3564 (2022/03/07)
An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is
Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction
Zhou, Wenjuan,Xu, Chenhao,Dong, Guanjun,Qiao, Hui,Yang, Jing,Liu, Hongmin,Ding, Lina,Sun, Kai,Zhao, Wen
, (2021/03/24)
Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.
Mechanochemical-Cascaded C-N Cross-Coupling and Halogenation Using N-Bromo- And N-Chlorosuccinimide as Bifunctional Reagents
Bera, Shyamal Kanti,Mal, Prasenjit
, p. 14144 - 14159 (2021/09/13)
Exploration of alternative energy sources for chemical transformations has gained significant interest from chemists, and mechanochemistry is one of those sources. Herein, we report the use of N-bromosuccinimides (NBS) and N-chlorosuccinimides (NCS) as bifunctional reagents for a cascaded C-N bond formation and subsequent halogenation reactions. Under the solvent-free mechanochemical (ball-milling) conditions, the synthesis of a wide range of phenanthridinone derivatives from N-methoxy-[1,1′-biphenyl]-2-carboxamides is accomplished. During the reactions, NBS and NCS first assisted the oxidative C-N coupling reaction and subsequently promoted a halogenation reaction. Thus, the role of NBS and NCS was established to be bifunctional. Overall, a mild, solvent-free, convenient, one-pot, and direct synthesis of various bromo- and chloro-substituted phenanthridinone derivatives was achieved.
