- Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels-Alder Cascade Reaction
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We describe here three alkynyl substituted naphthalenes that display promising luminescence characteristics. Each compound is easily and efficiently synthesized in three steps by capitalizing on the hexadehydro-Diels-Alder (HDDA) cycloisomerization reacti
- Xu, Feng,Hershey, Kyle W.,Holmes, Russell J.,Hoye, Thomas R.
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- Design, Synthesis, and Bioactivities of Phthalide and Coumarin Derivatives Based on the Biosynthesis and Structure Simplification of Gossypol
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Because gossypol and hemigossypol show antiviral activity but are structurally complex, we designed and synthesized a series of structurally simpler phthalide and coumarin derivatives. The phthalide derivatives were synthesized by opening the naphthalene ring of hemigossypol, and the coumarin derivatives were synthesized by ring-opening reactions of the phthalide derivatives with the goal of investigating the effect of the lactone ring size on bioactivity. The bioassay results showed that the two series of target compounds possessed moderate to good activities against tobacco mosaic virus, One of the compounds showed in vivo inactivation, curative, and protection activities of 50 ± 1, 53 ± 3, and 48 ± 2% at 500 mg/L, values which are higher than those of gossypol (32 ± 1, 35 ± 1, 29 ± 1%, respectively) and comparable to those of hemigossypol (55 ± 1, 49 ± 1, and 48 ± 1%, respectively) and the commercial antiviral agent ningnanmycin (56 ± 2, 54 ± 1, 58 ± 1%) at the same dose. Thus, this compound is a promising candidate for the development of new anti-plant-virus agents. In addition, most of the synthesized compounds showed broad-spectrum activity when tested against 14 kinds of phytopathogenic fungi and showed selectivity against Sclerotinia sclerotiorum, Physalospora piricola, and Rhizoctonia cerealis. Moreover, some of the compounds exhibited activity against Plutella xylostella larvae; the two most active compounds exhibited larvicidal activities (LC50) of 4.10 and 5.47 mg/L, respectively. Further studies showed that these compounds also exhibited insecticidal activities against Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis larvae.
- Guo, Zhonglin,Zhou, Pan,Song, Hongjian,Liu, Yuxiu,Zhang, Jingjing,Li, Yongqiang,Wang, Qingmin
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p. 15123 - 15135
(2021/12/27)
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- Copper-Catalyzed Photoinduced Enantioselective Dual Carbofunctionalization of Alkenes
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A photoinduced, copper-catalyzed, highly enantioselective dual alkylation/arylation and alkynylation of alkene is reported. A single chiral copper(I) complex serves to enable photoredox catalysis and induce enantioselectivity during the reaction. This reaction couples three different components under mild reaction conditions, exhibits a broad substrate scope, and provides facile access to chiral propargylic systems, including those featuring valuable fluorinated substituents.
- Chen, Bin,Li, Chen,Sun, Youwen,Xu, Meichen,Zhang, Dayong,Zhang, Guozhu,Zhang, Yajing
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supporting information
(2020/02/28)
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- Electrochemical synthesis of copper(i) acetylides: Via simultaneous copper ion and catalytic base electrogeneration for use in click chemistry
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We report an efficient and sustainable electrochemical synthesis of copper(i) acetylides using simultaneous copper oxidation and Hofmann elimination of quaternary ammonium salts. The electrochemically-generated base was also regenerated electrochemically,
- Seavill, Peter W.,Holt, Katherine B.,Wilden, Jonathan D.
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p. 29300 - 29304
(2019/09/30)
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- Direct Metal-Free Entry to Aminocyclobutenes or Aminocyclobutenols from Ynamides: Synthetic Applications
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The [2+2] cycloaddition of ynamides with the highly polarized reagent Tf2C=CH2has been developed to regioselectively afford bis(triflyl)aminocyclobutenes in the absence of catalyst under mild conditions. Incidentally, with the ynamides bearing electron-rich aromatic rings at the C-terminal, an interesting reactivity switch was observed; a cyclization/hydroxylation sequence yielded 2-amino-3-(triflyl)cyclobut-2-enols. Aminocyclobutene construction with addition of alcohols resulted in the formation of aminocyclobutenyl ethers through a cyclization/hydroalkoxylation process. Moreover, the utility of functionalized aminocyclobutenes as precursors for further elaboration was demonstrated with the preparation of α-amino-β,γ-unsaturated ketones and 3-(triflyl)buta-1,3-dien-2-amines through 4 π-electrocyclic ring opening.
- Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos
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supporting information
p. 8998 - 9005
(2016/07/06)
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- Room-Temperature Alkynylation of Phosphine Oxides with Copper Acetylides: Practical Synthesis of Alkynylphosphine Oxides
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An efficient procedure for the synthesis of alkynylphosphine oxides based on the oxidative alkynylation of secondary phosphine oxides with copper acetylides was developed. Activation with molecular oxygen in the presence of either a mixture of 1,2-dimethylimidazole and triethylamine or N-methylimidazole alone enabled the formal umpolung of the poorly nucleophilic copper acetylides, which were coupled with phosphine oxides under remarkably mild conditions. Notable features of this procedure are the availability of the starting materials, its user-friendliness, and its mild conditions, which allow the synthesis of complex alkynylphosphine oxides.
- Gérard, Phidéline,Veillard, Romain,Alayrac, Carole,Gaumont, Annie-Claude,Evano, Gwilherm
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p. 633 - 638
(2017/01/18)
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- Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes
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A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.
- Chen, Wenwen,Wang, Bo,Liu, Nan,Huang, Dayun,Wang, Xinyan,Hu, Yuefei
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supporting information
p. 6140 - 6143
(2015/01/09)
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- From bis(silylene) and bis(germylene) pincer-type nickel(II) complexes to isolable intermediates of the nickel-catalyzed sonogashira cross-coupling reaction
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The first [ECE]Ni(II) pincer complexes with E = SiII and E = GeII metallylene donor arms were synthesized via C-X (X = H, Br) oxidative addition, starting from the corresponding [EC(X)E] ligands. These novel complexes were fully characterized (NMR, MS, and XRD) and used as catalyst for Ni-catalyzed Sonogashira reactions. These catalysts allowed detailed information on the elementary steps of this catalytic reaction (transmetalation → oxidative addition → reductive elimination), resulting in the isolation and characterization of an unexpected intermediate in the transmetalation step. This complex, {[ECE]Ni acetylide → CuBr} contains both nickel and copper, with the copper bound to the alkyne π-system. Consistent with these unusual structural features, DFT calculations of the {[ECE]Ni acetylide → CuBr} intermediates revealed an unusual E-Cu-Ni three-center-two-electron bonding scheme. The results reveal a general reaction mechanism for the Ni-based Sonogashira coupling and broaden the application of metallylenes as strong σ-donor ligands for catalytic transformations.
- Gallego, Daniel,Brueck, Andreas,Irran, Elisabeth,Meier, Florian,Kaupp, Martin,Driess, Matthias,Hartwig, John F.
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p. 15617 - 15626
(2013/11/06)
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- Unprecedented synthesis of alkynylphosphine-boranes through room-temperature oxidative alkynylation
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An original and user-friendly synthesis of alkynylphosphine-boranes, useful building blocks in organic synthesis, based on an oxidative P-alkynylation reaction with readily available copper acetylides is reported. The ability of a secondary phosphine protected with a borane to undergo oxidative coupling without oxidation of the P-moiety is demonstrated for the first time. The reaction, which proceeds at room temperature, is applicable to the preparation of enantioenriched and structurally complex alkynylphosphine-boranes.
- Jouvin, Kevin,Veillard, Romain,Theunissen, Cedric,Alayrac, Carole,Gaumont, Annie-Claude,Evano, Gwilherm
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supporting information
p. 4592 - 4595
(2013/09/24)
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- RECEPTOR FUNCTION CONTROLLING AGENT
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The GPR40 receptor function regulator of the present invention, which comprises a compound having an aromatic ring and a group capable of releasing cation is useful as an insulin secretagogue or an agent for the prophylaxis or treatment of diabetes and the like.
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Page/Page column 86; 87
(2008/06/13)
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- Synthesis of diphenylacetylenes containing donor and acceptor substituents with 4′-formyl-4-methoxydiphenylacetylene as an example
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A method for the synthesis of diphenylacetylenes containing donor and acceptor groups in aryl substituents was proposed. 4′-Formyl-4- methoxydiphenylacetylene was synthesized as an example.
- Gonzalez-Rojas,Oprunenko,Morales
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p. 474 - 475
(2007/10/03)
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- Substituted benzofurans and benzothiophenes
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The compounds are benzoyl benzofurans and benzothiophenes having pharmacological activity, in particular, coronary vasodilator activity useful for the treatment of angina pectoris and intermediates for the preparation thereof.
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