6938-06-3Relevant articles and documents
Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua
, p. 68 - 74 (2021/11/16)
Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]
Zr-MOF-808 as Catalyst for Amide Esterification
Villoria-del-álamo, Beatriz,Rojas-Buzo, Sergio,García-García, Pilar,Corma, Avelino
supporting information, p. 4588 - 4598 (2020/12/25)
In this work, zirconium-based metal–organic framework Zr-MOF-808-P has been found to be an efficient and versatile catalyst for amide esterification. Comparing with previously reported homogeneous and heterogeneous catalysts, Zr-MOF-808-P can promote the reaction for a wide range of primary, secondary and tertiary amides with n-butanol as nucleophilic agent. Different alcohols have been employed in amide esterification with quantitative yields. Moreover, the catalyst acts as a heterogeneous catalyst and could be reused for at least five consecutive cycles. The amide esterification mechanism has been studied on the Zr-MOF-808 at molecular level by in situ FTIR spectroscopic technique and kinetic study.
IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway
Talukdar, Ranadeep
supporting information, p. 5303 - 5308 (2020/04/17)
An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.
Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas
Pandey, Ganesh,Koley, Suvajit,Talukdar, Ranadeep,Sahani, Pramod Kumar
supporting information, p. 5861 - 5865 (2018/09/21)
A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.
Synthesis and structures of 1,2,4-triazoles derivatives
Wang, Ning,Sheng, Jun-Feng,Song, Fei,Tong, Yu-Zhu,Wang, Zuo-Xiang
, p. 746 - 751 (2015/05/05)
Abstract A series of novel 1,2,4-triazole derivatives were synthesized, and their structures were characterized by IR, UV-Vis, FL, NMR, ESI-MS, and elemental analysis. In the meanwhile, the single crystal structures of 3,4-diethyl-5-(4-pyridyl)-1,2,4-triazole and 3,4-dimethyl-5-(o-hydroxyphenyl)-1,2,4-triazole were determined by X-ray diffraction.
Ionic liquids provide unique opportunities for oral drug delivery: Structure optimization and in vivo evidence of utility
Williams, Hywel D.,Sahbaz, Yasemin,Ford, Leigh,Nguyen, Tri-Hung,Scammells, Peter J.,Porter, Christopher J. H.
supporting information, p. 1688 - 1690 (2014/02/14)
Ionic liquids (ILs) have been exploited to improve the absorption of poorly water-soluble drugs. Custom-made ILs solubilized very high quantities of the poorly water-soluble drugs, danazol and itraconazole, and maintained drug solubilization under simulated gastro-intestinal conditions. A danazol-containing self-emulsifying IL formulation gave rise to 4.3-fold higher exposure than the crystalline drug and prolonged exposure compared with a lipid formulation.
LUBRICANT COMPOSITIONS CONTAINING A HETEROAROMATIC COMPOUND
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, (2016/04/21)
An ashless additive for lubricating oil compositions, lubricating oil compositions and methods for lubricating that are effective to improve the total base number (TBN) of a lubricant composition. The additive is a reaction product of a compound of the formula: with NH3, an alcohol, an amine, or a hydrocarbyl amine, wherein R1 is selected from H, a hydrocarbyl group, the alcohol or amine contains from 1 to about 24 carbon atoms, and the hydrocarbyl amine has a number average molecular weight ranging from about 100 to about 6000
Ligand free palladium catalyzed decarboxylative cross-coupling of aryl halides with oxalate monoester salts
Li, Yan,Chen, Huan-Huan,Wang, Chu-Fei,Xu, Xiao-Lan,Feng, Yi-Si
, p. 5796 - 5799 (2012/10/29)
Ligand free Pd-catalyzed decarboxylative cross-coupling of potassium oxalate monoester and derivatives with aryl iodides and bromides is described. Functionalized aromatic esters can be efficiently synthesized via this method with only 1.0 mol % Pd(OAc)2 catalyst without any phosphine ligand. This method illustrates an inexpensive and operationally simple method for the preparation of aromatic esters and acids, which is especially beneficial for a large scale synthesis.
Efficient carbonylation of aryl and heteroaryl bromides under atmospheric pressure of CO
Yang, Weizhun,Han, Wei,Zhang, Weidong,Shan, Lei,Sun, Jiansong
supporting information; experimental part, p. 2253 - 2255 (2011/10/19)
In the presence of Et and n-BuOH, efficient alkoxycarbonylation of (hetero)aromatic bromides was achieved under atmospheric pressure of carbon monoxide with in situ generated palladium/rac-BINAP as catalyst. Georg Thieme Verlag Stuttgart - New York.
An improved protocol for palladium-catalyzed alkoxycarbonylations of aryl chlorides with alkyl formates
Schareina, Thomas,Zapf, Alexander,Cotte, Alain,Gotta, Matthias,Beller, Matthias
experimental part, p. 1205 - 1209 (2010/07/04)
The palladium-catalyzed alkoxycarbonylation of aryl and heteroaryl halides using butyl formate has been investigated. In the presence of palladium (II) acetate/n-butylbis(1-adamantyl)phosphine (L1), and l,8-diazabicyclo[5.4.0]undec- 7-ene (DBU) as base fo
