- Metal-free cross-dehydrogenative coupling of aryl aldehydes to give symmetrical carboxylic anhydrides promoted by the TBHP/nBu4PBr system
-
A novel, efficient, and metal-free dual C–O bond formation reaction for the synthesis of carboxylic anhydrides from aryl aldehydes via cross-dehydrogenative coupling is described. Heating a mixture of aromatic aldehydes and an aqueous solution of tert-butyl hydroperoxide as oxidant in the presence of catalytic nBu4PBr in chlorobenzene at 80?°C for 3?h afforded the corresponding carboxylic anhydrides in good to excellent yields.
- Adib, Mehdi,Pashazadeh, Rahim,Rajai-Daryasarei, Saideh,Mirzaei, Peiman,Jamal Addin Gohari, Seyed
-
-
Read Online
- Cu-MOF: An efficient heterogeneous catalyst for the synthesis of symmetric anhydrides: Via the C-H bond activation of aldehydes
-
In this paper, an efficient and straightforward synthetic approach for the preparation of a number of symmetric carboxylic anhydrides was reported using Cu2(BDC)2(DABCO) as an efficient heterogeneous catalyst via the C-H bond activation of aldehydes with excellent yields and simple work up. This C-H bond activation reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents. The Cu-MOF catalyst was recycled and reused four times without any loss of catalytic activity.
- Ahmadzadeh, Zahra,Mokhtari, Javad,Rouhani, Morteza
-
p. 24203 - 24208
(2018/07/25)
-
- One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
-
In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.
- Liao, Yen-Sen,Liang, Chien-Fu
-
supporting information
p. 1871 - 1881
(2018/03/23)
-
- An investigation on practical synthesis of carboxylic acid derivatives using p-toluenesulfonyl chloride
-
Carboxylic acid derivatives are well recognized as important class of reagents frequently used in the preparation of a variety of fine or special chemicals such as amides, esters, peptides, drugs, and dyes. Although several methods were developed for the preparation of these compounds, many of them present difficulties, including low yield, high reaction temperature, harsh reaction conditions, tedious work-up, and incompatibility with scale-up. Methods: The synthesis of carboxylic anhydrides is developed through the reaction of carboxylic acids with TsCl in the presence of K2CO3 and acetonitrile as a solvent under ultrasound irradiation and conventional conditions. In addition, one-pot synthesis of acyl azides was carried out in the presence of produced carboxylic anhydrides and the addition of sodium azide under identical condition. Results: A series of carboxylic anhydrides and acyl azides were synthesized using TsCl under ultrasound irradiation and conventional stirring with simple procedure, mild reaction conditions, high yields, and scale-up ability without any restriction. In most cases, the reaction under ultrasound irradiation was better in both yields and the reaction times compared to the conventional method. Conclusion: A convenient method has been developed for the preparation of carboxylic anhydrides and acyl azides under ultrasound irradiation and conventional stirring. The present method is practical and a highly effective alternative for previous reports. The major advantages of this method are: (i) simplicity of the procedure (ii) high yields and high purity of product (iii) scale-up capacity without considerable limitation in conventional system. Under ultrasound irradiation short reaction times as compared to conventional method are observed; yields are comparable to or better than conventional method.
- Eskandari, Parvin,Kazemi, Foad
-
p. 431 - 439
(2017/07/24)
-
- Cu(I) catalyzed synthesis of anhydrides from aldehydes via CDC-pathway at ambient temperature
-
A one-pot simple and concise methodology has been developed for synthesizing aromatic carboxylic anhydrides starting from easily accessible aromatic aldehydes using cuprous chloride as the catalyst and TBHP as the oxidant in DMSO solvent to garner moderate to good yields via radical pathway in short and convenient reaction time at room temperature.
- Nuree, Yasin,Singha, Raju,Ghosh, Munmun,Roy, Pronay,Ray, Jayanta K.
-
supporting information
p. 1479 - 1482
(2016/03/12)
-
- TBHP-promoted and iodide-catalyzed synthesis of anhydrides via cross dehydrogenative coupling (CDC) of aldehydes
-
We have successfully developed a transition metal free green methodology for the synthesis of carboxylic anhydrides from aldehydes via CDC pathway and have also demonstrated the reaction mechanism. The developed method has also been successfully applied for the synthesis of amides.
- Singha, Raju,Ghosh, Munmun,Nuree, Yasin,Ray, Jayanta K.
-
supporting information
p. 1325 - 1327
(2018/03/29)
-
- Synthesis of symmetric anhydrides using visible light-mediated photoredox catalysis
-
A new approach to anhydride formation is reported via activation of C-O bonds by the Vilsmeier-Haack reagent formed by Ru(bpy)3Cl2 and CBr4 in DMF. Various aryl and alkyl carboxylic acids are converted to the corresponding anhydrides in excellent yields.
- Konieczynska, Marlena D.,Dai, Chunhui,Stephenson, Corey R. J.
-
supporting information; experimental part
p. 4509 - 4511
(2012/07/31)
-
- Carboxylic acid anhydrides via Pd-catalyzed carbonylation of aryl halides at atmospheric CO pressure
-
A convenient method has been developed, which allows for the direct transformation of aryl iodides into the corresponding carboxylic acid anhydrides via Pd-catalyzed carbonylation under atmospheric CO pressure. The Royal Society of Chemistry 2012.
- Li, Yang,Xue, Dong,Wang, Chao,Liu, Zhao-Tie,Xiao, Jianliang
-
supporting information; experimental part
p. 1320 - 1322
(2012/02/04)
-
- Substrate activity screening: A fragment-based method for the rapid identification of nonpeptidic protease inhibitors
-
A new fragment-based method for the rapid development of novel and distinct classes of nonpeptidic protease inhibitors, Substrate Activity Screening (SAS), is described. This method consists of three steps: (1) a library of N-acyl aminocoumarins with diverse, low molecular weight N-acyl groups is screened to identify protease substrates using a simple fluorescence-based assay, (2) the identified N-acyl aminocoumarin substrates are optimized by rapid analogue synthesis and evaluation, and (3) the optimized substrates are converted to inhibitors by direct replacement of the aminocoumarin with known mechanism-based pharmacophores. The SAS method was successfully applied to the cysteine protease cathepsin S, which is implicated in autoimmune diseases. Multiple distinct classes of nonpeptidic substrates were identified upon screening an N-acyl aminocoumarin library. Two of the nonpeptidic substrate classes were optimized to substrates with >8000-fold improvements in cleavage efficiency for each class. Select nonpeptidic substrates were then directly converted to low molecular weight, novel aldehyde inhibitors with nanomolar affinity to cathepsin S. This study demonstrates the unique characteristics and merits of this first substrate-based method for the rapid identification and optimization of weak fragments and provides the framework for the development of completely nonpeptidic inhibitors to many different proteases.
- Wood, Warren J. L.,Patterson, Andrew W.,Tsuruoka, Hiroyuki,Jain, Rishi K.,Ellman, Jonathan A.
-
p. 15521 - 15527
(2007/10/03)
-
- A Cheap, Simple and Efficient Method for the Preparation of Symmetrical Carboxylic Acid Anhydrides
-
A manipulatively simple and facile one-pot procedure for the synthesis of symmetrical anhydride is reported. Treatment of carboxylic acids with tosyl chloride in K2CO3 media under solvent free conditions gives the corresponding anhydrides in good to excellent yields in a short reaction time via carboxylic sulfonic anhydride as the key intermediate.
- Kazemi, Foad,Sharghi, Hashem,Nasseri, Mohammad Ali
-
p. 205 - 207
(2007/10/03)
-
- An efficient and simple procedure for preparation of esters and anhydrides from acid chlorides in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) under solvent-free conditions
-
A manipulatively one-pot and rapid method for the synthesis of aliphatic and aromatic ester and anhydride from acid chloride and alcohol or potassium salt of carboxylic acid under solvent-free conditions is reported. The reaction has been carried out in excellent yield and short reaction time in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) under solvent-free conditions.
- Hajipour,Mazloumi
-
-
- A facile synthesis of acid anhydrides
-
A facile synthesis of symmetric and unsymmetric acid anhydrides using phase-transfer catalysis is described. By this method different types of anhydrides can be obtained in high yields under mild conditions even on microscale levels.
- Dubey,Kumar, R. Vinod
-
-
- Palladium-promoted One-step Synthesis of Aromatic Acid Anhydrides from Aromatic Compounds with Carbon Monoxide
-
The one-step synthesis of aromatic acid anhydrides from aromatic compounds such as benzene, toluene, anisole, chlorobenzene, furan, and thiophen has been carried out using carbon monoxide, 1,2-dibromoethane, and palladium acetate
- Fujiwara, Yuzo,Kawata, Itaru,Kawauchi, Tomio,Taniguchi, Hiroshi
-
p. 132 - 133
(2007/10/02)
-