4153-45-1Relevant academic research and scientific papers
One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling
Wu, Hongxiang,Xu, Baiping,Li, Yue,Hong, Fengying,Zhu, Dezhao,Jian, Junsheng,Pu, Xiaoer,Zeng, Zhuo
, p. 2987 - 2992 (2016/04/26)
A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min. (Chemical Equation Presented).
Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones
Hao, Wenyan,Liu, Haiyi,Yin, Lin,Cai, Mingzhong
, p. 4244 - 4251 (2016/06/09)
A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.
Palladacycle-Catalyzed Carbonylative Suzuki-Miyaura Coupling with High Turnover Number and Turnover Frequency
Gautam, Prashant,Bhanage, Bhalchandra M.
, p. 7810 - 7815 (2015/08/18)
This work reports the carbonylative Suzuki-Miyaura coupling of aryl iodides catalyzed by palladacycles. More importantly, the palladacycles have been used to generate high turnover numbers (TON's) and turnover frequencies (TOF's). A range of aryl iodides can be coupled with arylboronic acids, generating TON's in the range of 106 to 107 and TOF's in the range of 105 to 106 h-1. Comparison of the palladacycles with a conventional palladium source shows their superiority in generating high TON's and TOF's.
TFAA/H3PO4-Mediated C-2 acylation of thiophene: A direct synthesis of known and novel thiophene derivatives of pharmacological interest
Bindu,Naini, Shravan Reddy,Shanmukha Rao,Dubey,Pal, Sarbani
, p. 586 - 593 (2014/06/10)
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.
The transition-metal-catalyst-free oxidative homocoupling of organomanganese reagents prepared by the insertion of magnesium into organic halides in the presence of MnCl2·2LiCl
Peng, Zhihua,Li, Na,Sun, Xinyang,Wang, Fang,Xu, Lanjian,Jiang, Cuiyu,Song, Linhua,Yan, Zi-Feng
, p. 7800 - 7809 (2014/12/10)
Organomanganese reagents were prepared by the insertion of magnesium into aryl halides in the presence of MnCl2·2LiCl. These organomanganese reagents smoothly undergo 1,2-addition, acylation, and Pd-catalyzed cross-coupling with various electrophiles. Especially, the oxidative homocoupling of organomanganese reagents was completed in one pot without an additional transition-metal catalyst.
A phosphane-free, atom-efficient cross-coupling reaction of triarylbismuths with acyl chlorides catalyzed by MCM-41-immobilized palladium complex
Zhao, Hong,Yin, Lin,Cai, Mingzhong
, p. 1337 - 1345 (2013/04/10)
The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuths and acyl chlorides was achieved in N-methylpyrrolidone (NMP) with Bu3N as the base at 80 °C in the presence of 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41-2N-Pd(OAc)2, MCM = mobile crystalline material] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields. This heterogeneous palladium catalyst exhibited a high activity, which was similar to that of Pd(PPh3)4. The catalyst can be recovered by a simple filtration of the reaction solution and recycled in at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of phosphane ligands, but also solves the basic problem of palladium catalyst recovery and reuse. The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuth compounds and acyl chlorides was achieved in N-methylpyrrolidone with Bu3N as the base at 80 °C in the presence of 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41-2N-Pd(OAc)2] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields. Copyright
Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes
Ushijima, Sousuke,Dohi, Souya,Moriyama, Katsuhiko,Togo, Hideo
experimental part, p. 1436 - 1442 (2012/03/09)
Aromatic ketones were efficiently prepared in good yields by the reactions of aryl bromides with n-BuLi, followed by the reactions with aromatic aldehydes or aliphatic aldehydes and the subsequent treatment with molecular iodine and K2CO3, in a one-pot method. The same treatment of arenes, instead of aromatic bromides, also provided the corresponding aromatic ketones in good yields. Using these methods, various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatics and electron-deficient aromatics could be prepared efficiently by a simple, transition-metal-free, and therefore environmentally benign experimental procedure.
Deprotonative metalation of aromatic compounds by using an amino-based lithium cuprate
Nguyen, Tan Tai,Marquise, Nada,Chevallier, Floris,Mongin, Florence
experimental part, p. 10405 - 10416 (2011/10/12)
Deprotonative cupration of aromatic compounds by using amino-based lithium cuprates was optimized with 2,4-dimethoxypyrimidine and 2-methoxypyridine as the substrates and benzoyl chloride as the electrophile. [(tmp)2CuLi] (+2 LiCl) (tmp=2,2,6,6-tetramethylpiperidino) was identified as the best reagent and its use was extended to anisole, 1,4-dimethoxybenzene, other substituted pyridines, furan, thiophene and derivatives, and N-Boc-indole (Boc=tert-butyloxycarbonyl). Of the electrophiles employed to attempt the interception of the generated aryl cuprates, aroyl chlorides, iodomethane, and diphenyl disulfide efficiently reacted. In addition, different oxidative agents were identified to afford symmetrical biaryls. Finally, palladium-catalyzed coupling with aryl halides was optimized and allowed the synthesis of different aryl derivatives in medium to good yields.
A phosphine-free carbonylative cross-coupling reaction of aryl iodides with arylboronic acids catalyzed by immobilization of palladium in MCM-41
Cai, Mingzhong,Peng, Jian,Hao, Wenyan,Ding, Guodong
experimental part, p. 190 - 196 (2011/03/20)
The phosphine-free heterogeneous carbonylative cross-coupling of aryl iodides with arylboronic acids under an atmospheric pressure of carbon monoxide was achieved in anisole at 80 °C in the presence of a 3-(2-aminoethylamino) propyl-functionalized MCM-41-immobilized palladium(ii) complex [MCM-41-2N-Pd(ii)], yielding a variety of unsymmetrical biaryl ketones in good to high yield. This heterogeneous palladium catalyst exhibited higher activity and selectivity than PdCl2(PPh3)2, can be recovered and recycled by a simple filtration of the reaction solution, and used for at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.
MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation
de Noronha, Rita G.,Fernandes, Ana C.,Rom?o, Carlos C.
experimental part, p. 1407 - 1410 (2009/06/18)
The use of MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation is described. A series of aromatic ketones and sulfones were prepared in moderate to good yields using acyl chloride or sulfonyl chloride in the presence of MoO2Cl2 (20 mol %), under solvent-free conditions.
