- Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage
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Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe
- Ma, Yangmin,Shao, Lei,Szostak, Michal,Wang, Ruihong,Zhang, Jin,Zhang, Pei
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supporting information
(2022/01/04)
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- Palladium nanoparticles supported on a titanium dioxide cellulose composite (PdNPs@TiO2-Cell) for ligand-free carbon-carbon cross coupling reactions
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Well-dispersed non-spherical PdNPs with a diameter of 39-45 nm supported on a TiO2-cellulose composite (PdNPs@TiO2-Cell) can be synthesized by a simple and clean route. The catalyst was well characterized by XRD, FE-SEM, EDS, and TEM techniques. The PdNPs have good dispersity on the TiO2-Cell support. This results in excellent catalytic activities for the synthesis of biphenyls, acrylates, acetylenes and prochiral ketones using low Pd loading (1 mol%) at comparatively low temperature. The effects of the nature and amount of bases, nature of solvents, amount of catalyst and the reaction temperature on the activity of PdNPs@TiO2-Cell were thoroughly investigated. The catalyst showed at least four times reusability without decrease in catalytic activity.
- Jadhav, Sanjay,Jagdale, Ashutosh,Kamble, Santosh,Kumbhar, Arjun,Salunkhe, Rajshri
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p. 3406 - 3420
(2016/01/25)
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- Preparation of acylthiophenes by iron(III) chloride catalyzed reactions of tris(2-thienyl)stibanes with acyl chlorides
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The reactions of tris(2-thienyl)stibanes with various acyl chlorides, using a catalytic amount of iron(III) chloride, afforded 2-acylthiophenes. Iron(III) chloride is presumed to act as a Lewis acid, and the ipso substituent of each 2-thienyl group of tris(2-thienyl)stibane is replaced with an acyl group. The reaction is highly atom-efficient in that all three thiophene rings of tris(2-thienyl)stibane take part in the reaction. The reaction procedure is so simple that it can also be carried out under solvent-free and aerobic conditions.
- Kakusawa, Naoki,Nakagawa, Yoshie,Toshima, Yutarou,Yasuike, Shuji,Kurita, Jyoji
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p. 1170 - 1175
(2015/07/15)
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- In situ generation of palladium nanoparticles: Ligand-free palladium catalyzed pivalic acid assisted carbonylative Suzuki reactions at ambient conditions
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Highly selective carbonylative Suzuki reactions of aryl iodides with arylboronic acids using an in situ generated nanopalladium system furnished products in high yields. The reactions were performed under ambient conditions and in the absence of an added ligand. The key to success is the addition of pivalic acid, which can effectively suppress undesired Suzuki coupling. The synthesis can be easily scaled up, and the catalytic system can be reused up to nine times. The nature of the active catalytic species are discussed.
- Zhou, Qing,Wei, Shaohua,Han, Wei
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p. 1454 - 1460
(2014/03/21)
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- TFAA/H3PO4-Mediated C-2 acylation of thiophene: A direct synthesis of known and novel thiophene derivatives of pharmacological interest
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A number of aliphatic and aromatic carboxylic acids were reacted with thiophene in the presence of trifluoroacetic anhydride and H3PO 4 to give a variety of acylated thiophenes in good to excellent yields. The methodology was used to prepare known nonsteroidal anti-inflammatory drug-based novel compounds of potential pharmacological significances. Molecular modeling studies were carried out by using nonsteroidal anti-inflammatory drug-based thiophene derivatives to assess their cyclooxygenase inhibiting potential in silico. On the basis of docking studies followed by subsequent in vitro assay, indomethacin-based thiophene derivative was identified as a novel cyclooxygenase-2 inhibitor with balanced selectivity.
- Bindu,Naini, Shravan Reddy,Shanmukha Rao,Dubey,Pal, Sarbani
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p. 586 - 593
(2014/06/10)
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- Friedel-crafts acylation of arenes with carboxylic acids using polystyrene-supported aluminum triflate
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Cross-linked polystyrene-supported aluminum triflate (Ps-Al(OTf) 3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds. The catalyst can be easily prepared from cheap starting materials, is stable (as a bench top catalyst) and is reusable.
- Boroujeni, Kaveh Parvanak,Parvanak, Kamran
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experimental part
p. 155 - 163
(2012/01/02)
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- Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3
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Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. tuebitak.
- Parvanak Boroujeni, Kaveh
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experimental part
p. 621 - 630
(2010/11/04)
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- Simple and efficient procedure for the friedel-crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/AL2O3 under heterogeneous conditions
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An efficient and chemoselective method for the Friedel-Crafts acylation of aromatic compounds using P2O5/Al2O3 and carboxylic acids. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones in good yields.
- Hajipour, Abdol R.,Zarei, Amin,Khazdooz, Leila,Ruoho, Arnold E.
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experimental part
p. 2702 - 2722
(2009/12/06)
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- Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 under heterogeneous conditions
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A convenient and efficient procedure for the Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 is described. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.
- Zarei, Amin,Hajipour, Abdol R.,Khazdooz, Leila
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scheme or table
p. 6715 - 6719
(2009/04/07)
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- Synthesis of 11C-/13C-Ketones by Suzuki Coupling
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Aryl triflates, methyl- or arylboronic acids, and a low concentration of [11C]carbon monoxide were employed on small scale in the syntheses of fifteen 11C-labelled ketones using palladium-mediated Suzuki coupling reactions. The reagents were confined in a micro-autoclave and heated at 150 °C for 5 min. The reaction required the presence of LiBr, but no additional base. The 11C-labelled products were obtained with decay-corrected radiochemical yields in the range 10-70% and with high specific radioactivity (150-640 GBq/μmol). The radiochemical purity of the final products exceeded 98%. One 13C-substituted ketone ([ 13C]-2′-benzonaphthone) was prepared and analysed by NMR spectroscopy for confirmation of the labelling position. The reference compound 2′-benzonaphthone was prepared by a palladium-catalysed reaction between sodium tetraphenylborate and 2-naphthoyl chloride. 2-Thienyl p-tolyl ketone, 4-nitrophenyl 2-thienyl ketone and 2-naphthyl 2-thienyl ketone were prepared by reactions between thiophene-2-boronic acid and the corresponding acid chlorides. The presented approach is novel and seems to be an efficient method for the synthesis of a wide range of 11C- as well as 13C-labelled ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Rahman, Obaidur,Kihlberg, Tor,Langstroem, Bengt
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p. 474 - 478
(2007/10/03)
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- Infrared and Nuclear Magnetic Resonance Properties of Benzoyl Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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Benzophenones, 2-benzoylthiophenes, 2-benzoylpyrroles, and 2-benzoylfurans, which have substituents at m- and p-positions of the benzoyl ring were prepared and their ir and nmr spectra were obtained in 0.1 M chloroform-d solution. The chemical shift values of each series were plotted against the Hammett substituent parameters to give good correlation, with the exception of the ortho-Hs and -Cs. The slopes as well as the differences in chemical shift gave sets of meaningful values for the indices of aromaticy.
- Jeon, Kyu Ok,Jun, Jung Ho,Yu, Ji Sook,Lee, Chang Kiu
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p. 763 - 771
(2007/10/03)
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- Synthesis of nitrobenzophenones from nitro-α-sulfonyldiphenylmethane derivatives
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α-Sulfonyl nitrodiphenylmethane derivatives undergo an autoxidation to nitrobenzophenones in the presence of solid K2CO3 and tetrabutylammonium bromide in dimethoxyethane in good yields.
- Wojciechowski, Krzysztof
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p. 135 - 144
(2007/10/03)
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- Benzylation via Tandem Grignard Reaction - Iodotrimethylsilane (TMSI) Mediated Reduction
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A method has been developed which allows for the large scale preparation of biarylmethanes.This method involves the initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI).A number of improvements over existing literature procedures are reported as well as previously unobserved dimerizations.Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not heteroaromatic.Mono-substituted alkanols react with TMSI to afford the corresponding iodides.A mechanistic study of the TMSI reduction is also reported.
- Stoner, Eric J.,Cothron, Darlene A.,Balmer, Mary K.,Roden, Brian A.
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p. 11043 - 11062
(2007/10/02)
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- Sulphonamides derived from diarylmethanes, the processes for preparing them and pharmaceutical compositions containing them
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The invention relates to new compounds corresponding to formula I: STR1 in which: W represents C=O, CH2 or CHOH, Z represents STR2 R1 and R2 represent especially Cl or F, R, R' and R" represent especially H, X represents especially CH2, Y represents especially COOH, u and v are two integers ranging from 0 to 10, p and q take the value 0 or 1, n and m are two integers ranging 0 to 10 and t is 0 or 1 the total number of carbon atoms in the chain STR3 ranging from 2 to 20, and to their physiologically acceptable salts obtained with organic or inorganic acids. These compounds are useful for preparing medicinal products which have, especially, anti-inflammatory properties.
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- Palladium-catalyzed acyldemetallation and carbonylation reactions of organomercurials for the synthesis of unsymmetrical ketones
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The palladium-catalyzed acyldemetallation reactions of organomercurials (R2Hg or AlkHgI) provide a mild, selective and general method for the synthesis of unsymmetrical heterocyclic ketones.High yields of ketones (RCOR') were obtained along with small amounts of homocoupling products (R2).The reaction is accelerated by a nucleophilic catalyst with both organic groups of R2Hg taking part in the reaction.The selectivity of the reaction towards the ketone can be increased by carrying out the reaction with a suitable combination of reactants under vacuum.The palladium-catalyzed carbonylation of organomercurials in the presence of ArI is another route to unsymmetrical ketones.The AlkHgI-ArI system undergoes carbonylation in the presence of palladium complex and excess iodide ion under mild conditions to give high yields of unsymmetrical ketones.The selectivity and rate of the reaction depend upon the nature of the catalyst, solvent and the concentration of iodide ion.
- Bumagin, N. A.,More, P. G.,Beletskaya, I. P.
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p. 379 - 388
(2007/10/02)
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