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
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.
N-(4-indolyl) N-heterocyclic carbene palladium complex and application thereof
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Paragraph 0095-0101, (2021/06/02)
The invention discloses N-(4-indolyl) N-heterocyclic carbene palladium complexes of which the chemical structural general formula is shown in the specification. The palladium complex provided by the invention can be used for catalyzing cross coupling reactions such as Suzuki-Miyaura coupling, Buchwald-Hartwig reaction and the like.