- AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: Synthesis of 3,3-diarylpropenenitriles
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Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr3, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3-
- Gorbunova, Yelizaveta,Ryabukhin, Dmitry S.,Vasilyev, Aleksander V.
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supporting information
p. 2663 - 2667
(2021/11/30)
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- Asymmetric Catalysis in Liquid Confinement: Probing the Performance of Novel Chiral Rhodium–Diene Complexes in Microemulsions and Conventional Solvents
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The role of liquid confinement on the asymmetric Rh catalysis was studied using the 1,2-addition of phenylboroxine (2) to N-tosylimine 1 in the presence of [RhCl(C2H4)2]2 and chiral diene ligands as benchmark reaction. To get access to Rh complexes of different polarity, enantiomerically pure C2-symmetric p-substituted 3,6-diphenylbicyclo[3.3.0]octadienes 4 and diastereomerically enriched unsymmetric norbornadienes 5 and 6 carrying either the Evans or the SuperQuat auxiliary were synthesized. A microemulsion containing the equal amounts of H2O/KOH and toluene/reactants was formulated using the hydrophilic sugar surfactant n-octyl β-d-glucopyranoside (C8G1) to mediate the miscibility between the nonpolar reactants and KOH, needed to activate the Rh–diene complex. Prominent features of this organized reaction medium are its temperature insensitivity as well as the presence of water and toluene-rich compartments with a domain size of 55 ? confirmed by small-angle X-ray scattering (SAXS). Although bicyclooctadiene ligands 4 a,b,e performed equally well under homogeneous and microemulsion conditions, ligands 4 c,d gave a different chemoselectivity. For norbornadienes 5, 6, however, microemulsions markedly improved conversion and enantioselectivity as well as reaction rate, as was confirmed by kinetic studies using ligand 5 b.
- Deimling, Max,Kirchhof, Manuel,Schwager, Barbara,Qawasmi, Yaseen,Savin, Alex,Mühlh?user, Tina,Frey, Wolfgang,Claasen, Birgit,Baro, Angelika,Sottmann, Thomas,Laschat, Sabine
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supporting information
p. 9464 - 9476
(2019/07/04)
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- Carbene-catalyzed LUMO activation of alkyne esters for access to functional pyridines
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A carbene-catalyzed LUMO activation of α,β-unsaturated alkyne esters is reported. This catalytic process allows for effective reactions of alkyne esters with enamides to synthesize functional pyridines via simple protocols. A previously unexplored unsaturated alkyne acyl azolium intermediate is involved in the key step of the reaction.
- Mou, Chengli,Wu, Jichang,Huang, Zhijian,Sun, Jun,Jin, Zhichao,Chi, Yonggui Robin
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p. 13359 - 13362
(2017/12/26)
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- Synthesis of 4-Arylidenepyrazolones by a Gold-Catalyzed Cyclization/Arylidene Group Transfer Cascade of N-Propioloyl Hydrazones
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An efficient gold-catalyzed cyclization/arylidene group transfer cascade reaction of N-propioloyl hydrazones has been developed. This method provides a novel approach for the synthesis of various functionalized 4-arylidenepyrazolones.
- Ding, Zong-Cang,Tang, Hai-Tao,Li, Ren-Hao,Ju, Lu-Chuan,Zhan, Zhuang-Ping
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p. 9307 - 9313
(2015/09/28)
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- Synthesis and fluorescence of the new environment-sensitive fluorophore 6-chloro-2,3-naphthalimide derivative
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Convenient and efficient synthesis of a new environmentally sensitive chlorine-substituted 2,3-naphthalimide-based fluorophore is reported. Benzotriazole carboxyl group activation of the 6-chloro-fluorophore enabled quick labeling of free and Fmoc-protected amino acids. The photophysical properties of the compounds obtained include high quantum yields in solvents of different polarity: water, methanol, acetonitrile and hexane.
- Katritzky, Alan R.,Ozcan, Sevil,Todadze, Ekaterina
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supporting information; experimental part
p. 1296 - 1300
(2010/06/15)
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- 14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and related opioids. Further examples of pseudoirreversible μ opioid receptor antagonists
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14β-4′-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the μ opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new liga
- Nieland, Nick P.R.,Rennison, David,Broadbear, Jillian H.,Purington, Lauren,Woods, James H.,Traynor, John R.,Lewis, John W.,Husbands, Stephen M.
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supporting information; experimental part
p. 6926 - 6930
(2010/04/28)
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- 2,5-diarylisothiazolone: Novel inhibitors of cytokine-induced cartilage destruction
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A series of 2,5-diarylisothiazolones is reported that inhibit the IL-1β- induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, n
- Wright, Stephen W.,Petraitis, Joseph J.,Freimark, Bruce,Giannaras, John V.,Pratta, Michael A.,Sherk, Susan R.,Williams, Jean M.,Magolda, Ronald L.,Arner, Elizabeth C.
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p. 851 - 858
(2007/10/03)
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- Flash Vacuum Pyrolysis of Stabilised Phosphorous Ylides. Part 4. Stepwise Construction of Terminal 1,3-Diynes, Conjugated Diacetylenic Esters and a Triacetylenic Ester
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Thirteen examples of stabilised alkynol ylides 6 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 500 deg C, to undergo extrusion of Ph3PO to give the diacetylenic esters 7 in moderate yield.At 750 deg C the same ylides afforded terminal 1,3-diynes 8 although often in poor yield.For R = 2-MeSC6H4 both 7 and 8 undergo secondary loss of Me* and cyclisation to give 2-alkynylbenzothiophene derivatives 9 and 10 in low yield.The first example of an alkadiynol ylide 11 has been prepared and is converted by FVP at 500 deg C into the triacetylenic ester 12.
- Aitken, R. Alan,Seth, Shirley
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p. 2461 - 2466
(2007/10/02)
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