- Pd-NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3-aroylquinolin-4 (1H)-one and acridone scaffolds
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We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd- NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like-COMe, -COOMe, -F, -Cl, -Br, -NH2, -CN) are well tolerated in this reaction. In addition, we have also demonstrated a new efficient route for the synthesis of biologically active and pharmaceutically important 2-substituted 3-Aroylquinolin-4(1H)-ones and acridone scaffolds.
- Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal
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- A synthesis of biaryl ketones via the C–S bond cleavage of thiol ester by a Cu/Ag salt
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We report the synthesis of biaryl ketones via an unprecedented copper/silver catalyzed acylative cross-coupling of thiol esters with either an arylboronic acid or a potassium aryltrifluoroborate. This new method proceeds without a requisite Pd-catalyst and Cu(I)TC mediator, and is efficient, versatile, operationally simple, and accommodating functionally diverse thiol esters, arylboronic acids, and potassium aryltrifluoroborates.
- Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal,Perl, Eliyahu
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p. 2751 - 2756
(2017/06/23)
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- Palladium-Catalyzed α-Arylation of Aryl Nitromethanes
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Catalytic conditions for the α-arylation of aryl nitromethanes have been discovered using parallel microscale experimentation, despite two prior reports of the lack of reactivity of these aryl nitromethane precursors. The method efficiently provides a variety of substituted, isolable diaryl nitromethanes. In addition, it is possible to sequentially append two different aryl groups to nitromethane. Mild oxidation conditions were identified to afford the corresponding benzophenones via the Nef reaction, and reduction conditions were optimized to afford several diaryl methylamines.
- Vangelder, Kelsey F.,Kozlowski, Marisa C.
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supporting information
p. 5748 - 5751
(2015/12/11)
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- 3-Mercapto-1,2,4-triazoles and N-acylated thiosemicarbazides as metallo-β-lactamase inhibitors
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The production of β-lactamases is an effective strategy by which pathogenic bacteria can develop resistance against β-lactam antibiotics. While inhibitors of serine-β-lactamases are widely used in combination therapy with β-lactam antibiotics, there are no clinically available inhibitors of metallo-β-lactamases (MBLs), and so there is a need for the development of such inhibitors. This work describes the optimisation of a lead inhibitor previously identified by fragment screening of a compound library. We also report that thiosemicarbazide intermediates in the syntheses of these compounds are also moderately potent inhibitors of the IMP-1 MBL from Pseudomonas aeruginosa. The interactions of these inhibitors with the active site of IMP-1 were examined using in silico methods.
- Faridoon,Hussein, Waleed M.,Vella, Peter,Islam, Nazar Ul,Ollis, David L.,Schenk, Gerhard,McGeary, Ross P.
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supporting information; experimental part
p. 380 - 386
(2012/02/04)
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- Copper-catalyzed arylation of arylboronic acids with aldehydes
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A novel copper-catalyzed arylation of arylboronic acids with aldehydes under oxygen atmosphere was achieved in the presence of Cu(OTf)2 and Xantphos, affording diaryl ketone derivatives in moderate to good yields. The efficiency of this reaction was demonstrated by the compatibility with fluoro, bromo, chloro, nitro, -methylsulfonyl, and trifluoromethyl groups. Georg Thieme Verlag Stuttgart ? New York.
- Zheng, Hanmei,Ding, Jinchang,Chen, Jiuxi,Liu, Miaochang,Gao, Wenxia,Wu, Huayue
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experimental part
p. 1626 - 1630
(2011/08/03)
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- Palladium-catalyzed reactions of arylboron compounds with carboxylic acid chlorides
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Reactions of sodium tetraarylborates and arylboronic acids with acyl chlorides in the presence of palladium salts afford non-symmetrical ketones in high yields under mild conditions.
- Korolev,Bumagin
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p. 364 - 369
(2007/10/03)
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- Antimony(V) chloride-benzyltriethylammonium chloride complex as an efficient catalyst for friedel-crafts acylation reactions
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A novel catalytic system, the complex of antimony(V) chloride (SbCl 5) and benzyltriethylammonium chloride (TEBA), C6H 5CH2NEt3(SbCl5)2Cl complex, is described for Friedel-Crafts acylation reactions of aromatics with acyl and sulfonyl chlorides. The catalyst has a number of useful characteristics, such as ready access, minimal toxicity, reusability, insensitivity to atmosphere and moisture, rapid acylation with high yield, and ease of operation.
- Huang, An-Ping,Liu, Xue-Yuan,Li, Lian-Hua,Wu, Xiao-Li,Liu, Wei-Min,Liang, Yong-Min
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p. 599 - 602
(2007/10/03)
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- Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes
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The cross-coupling reaction of sodium tetra-arylborates with acyl chlorides to give high yields of unsymmetric ketones has been carried out at 20°C in the presence of Pd(OAc)2 and Na2CO3 in dry or aqueous acetone. Under aqueous conditions arylboronic acids react smoothly with benzoyl chloride resulting in substituted benzophenones.
- Bumagin, Nikolay A.,Korolev, Dmitriy N.
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p. 3057 - 3060
(2007/10/03)
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- Utility of Complementary Molecular Reactivity and Molecular Recognition (CMR/R) Technology and Polymer-Supported Reagents in the Solution-Phase Synthesis of Heterocyclic Carboxamides
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The use of our recently reported chemical library purification strategy in the development of a herbicidal lead, N-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl-1H-pyrazole-5-carboxamide (3), is described. The approach applying fundamental properties of complementary molecular reactivity and molecular recognition (CMR/R) as the basis for a general purification strategy was utilized. Polymeric reagents were used in the synthesis to generate reactive species involved in product formation, and complementary molecular reactivity/molecular recognition polymer 8 (CMR/R polymer 8) was used in the solution-phase syntheses of building blocks, primary libraries, and lead refinement libraries. An extension of the CMR/R methodology was applied, utilizing a sequestration enabling reagent (SER), transforming a reactant into an electrophilic species sequestrable by CMR/R polymer 8. This library purification strategy enabled rapid lead generation and lead refinement to afford herbicide 27o. The CMR/R solid-phase purification technique enabled a simple, general, and powerful protocol, eliminating the usual tedious and time-consuming methods required for solution-phase product purification. The result was the synthesis of hundreds of compounds, prepared in a relatively short time, leading to a compound with a 4-fold improvement in herbicidal activity over the initial lead.
- Parlow, John J.,Mischke, Deborah A.,Woodard, Scott S.
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p. 5908 - 5919
(2007/10/03)
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- STUDIES IN TRIFLUOROMETHANESULPHONIC ACID-IV KINETICS AND MECHANISM OF ACYLATION OF AROMATIC COMPOUNDS
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A detailed kinetic study has been made of acylation reactions in solvent trifluoromethane sulphonic acid (CF3SO3H) using carboxylic acids as the electrophilic species involved.These species were shown to be probably the protonated form of the mixed anhydride.The reactions show high substrate selectivity characterised by high negative values of p+.Substituents in the carboxylic acids have a relatively small influence on the reactions rates due to a cancellation of substituents effects on the protonation of the mixed anhydride with those operating on the subsequent slow reaction of these species with the aromatic substrate.Anomalous effects were found for certain ortho substituents.The overall mechanism is discussed in terms of polar and steric effects in conjunction with the competing protonation of the aromatic bases, together with evidence from isotope effects.
- Roberts, R. M. G.,Sadri, A. R.
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p. 137 - 142
(2007/10/02)
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