6315-11-3Relevant academic research and scientific papers
Environmentally sustainable production and application of acyl phosphates
Cai, Hu,Fu, Zhengjiang,Guo, Shengmei,Li, Sen,Liang, Zhibin,Yan, Wenjie
supporting information, p. 7343 - 7347 (2020/11/19)
A versatile and environmentally friendly synthetic method for the formation of acyl phosphates is reported. By employing electrochemical oxidative dehydrogenative coupling, this transformation features a broad range of substrates, as well as metal-free, o
Supramolecular Pd(II) complex of DPPF and dithiolate: An efficient catalyst for amino and phenoxycarbonylation using Co2(CO)8 as sustainable C1 source
Gaikwad, Vinayak V.,Mane, Pravin A.,Dey, Sandip,Patel, Divya,Bhanage, Bhalchandra M.
, (2019/11/28)
Highly active, efficient and robust “dppf ligated tetranuclear palladium dithiolate complex” was synthesized and applied as a catalyst for chemical fixation of carbon monoxide for the synthesis value added chemicals such as tertiary amide and aromatic esters. The synthesized catalyst was characterized using different analytical techniques such as elemental analysis, 1H and 31P NMR spectroscopy. The use of Co2(CO)8 as a cheap, less toxic and low melting solid surrogate are additional advantages over the current protocol. The catalyst showed superior activity towards the Amino (10?3 mol % catalyst) and Phenoxycarbonylation (10-2 mol % catalyst) and high TON (104 to 103) and TOF (103 to 102 h-1). The Betol and Lintrin (active drug molecules) were synthesized under an optimized reaction condition. The scalability of the current protocol has been demonstrated up-to the gram level.
Sunlight assisted direct amide formation: Via a charge-transfer complex
Cohen, Irit,Mishra, Abhaya K.,Parvari, Galit,Edrei, Rachel,Dantus, Mauricio,Eichen, Yoav,Szpilman, Alex M.
supporting information, p. 10128 - 10131 (2017/09/23)
We report on the use of charge-transfer complexes between amines and carbon tetrachloride, as a novel way to activate the amine for photochemical reactions. This principle is demonstrated in a mild, transition metal free, visible light assisted, dealkylative amide formation from feedstock carboxylic acids and amines. The low absorption coefficient of the complex allows deep light penetration and thus scale up to a gram scale.
Preparation method of aryl amide compound and purification method thereof
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Paragraph 0020; 0021, (2017/05/02)
The invention discloses a preparation method for synthesis of an aryl amide compound and a purification method. The preparation method comprises the following steps: various aryl iodides and alkyl primary amine, alkyl secondary amine or alkyl tertiary ami
Carbonylative Tertiary Amide Synthesis from Aryl Iodides and Tertiary Amines via Oxidant-Free C?N Bond Cleavage Catalyzed by Palladium(II) Chloride in Polyethylene Glycol/Water
Mane, Rajendra S.,Bhanage, Bhalchandra M.
, p. 2621 - 2629 (2017/08/16)
In this work, we have described the carbonylative synthesis of amides from aryl iodides and tertiary amines as an aminal source via oxidant-free C(sp3)?N bond cleavage using in situ formation of palladium(0) nanoparticles from palladium(II) chloride in polyethylene glycol 400/water. Notably, these reactions were performed under base-free, ligand-free conditions and do not require any oxidant for the C?N bond cleavage. The developed protocol offers the selective N-dealkylation of tertiary amines in a polyethylene glycol/water solvent system. Numerous symmetrical and unsymmetrical aliphatic, alicyclic, benzyl, as well as aromatic tertiary amines with aryl iodides were well tolerated and afforded the desired products in good yields. Furthermore, the in situ generation of palladium(0) nanoparticles in the polyethylene glycol 400 was confirmed by TEM, FEG-SEM, EDS and XRD techniques, which strongly indicate that the palladium nanoparticles are highly active species and the reaction proceeds through the classical palladium(0)/palladium(II) pathway. Additionally, the syntheses can be easily scaled up and the catalytic system can be recycled up to five times without loss of its catalytic activity and selectivity. (Figure presented.).
A novel Pd-catalyzed N-dealkylative carbonylation of tertiary amines for the preparation of amides
Fang, Tao,Gao, Xu-Hong,Tang, Ri-Yuan,Zhang, Xing-Guo,Deng, Chen-Liang
supporting information, p. 14775 - 14777 (2014/12/11)
A novel and convenient protocol for the formation of amides via palladium-catalyzed N-dealkylative carbonylation of alkyl tertiary amines has been developed. In the presence of PdCl2(PhCN)2, CuO, PhCN and CO, a range of substituents on both aryl iodides and alkyl tertiary amines were compatible with the reaction to afford a series of N,N-disubstituted amides in moderate to excellent yields. This journal is
Microwave-promoted aminocarbonylation of aryl triflates using Mo(CO)6 as a solid CO source
Odell, Luke R.,S?vmarker, Jonas,Larhed, Mats
scheme or table, p. 6115 - 6118 (2009/04/04)
Palladium-catalyzed carbonylations of aryl triflates with a range of nucleophiles using Mo(CO)6 as a solid CO source were explored. The reactions proceeded smoothly providing moderate to good yields of the corresponding aryl amides, esters, or acylsulfonamides after only 20 min of microwave irradiation. The acyl transfer reagent 4-dimethylaminopyridine was found to promote some of the more difficult transformations.
Palladium-catalyzed aminocarbonylation of aryl chlorides at atmospheric pressure: The dual role of sodium phenoxide
Martinelli, Joseph R.,Clark, Thomas P.,Watson, Donald A.,Munday, Rachel H.,Buchwald, Stephen L.
, p. 8460 - 8463 (2008/09/18)
(Chemical Equation Presented) No pressure, no worries: A general, functional-group-tolerant, mild system for the Pd-catalyzed carbonylation of aryl chlorides to the corresponding amides has been developed. The catalyst operates at 1 atm CO using an inexpensive, air-stable, and commercially available ligand (see scheme, Cy = cyclohexyl). Sodium phenoxide is a critical additive in this transformation; its role has been studied using in situ IR spectroscopy.
Palladium-catalyzed cross-coupling reaction of arylboronic acids with chloroformate or carbamoyl chloride
Duan, Ya-Zhen,Deng, Min-Zhi
, p. 355 - 357 (2007/10/03)
The first palladium-catalyzed cross-coupling reaction between substituted arylboronic acids and chloroformate or carbamoyl chloride is described. One-carbon homologation from arylboronic acids was achieved to give corresponding esters or amides in good yi
Microwave-enhanced aminocarbonylations in water
Wu, Xiongyu,Larhed, Mats
, p. 3327 - 3329 (2007/10/03)
(Chemical Equation Presented) Aryl bromides can be rapidly converted to the corresponding secondary and tertiary benzamides in water. By using Mo(CO) 6 as the source of carbon monoxide, aminocarbonylations were conducted under air after only 10
