7464-43-9Relevant academic research and scientific papers
Direct synthesis of amides and imines by dehydrogenative homo or cross-coupling of amines and alcohols catalyzed by Cu-MOF
Anbardan, Soheil Zamani,Bozcheloei, Abolfazl Hassani,Mokhtari, Javad,Yari, Ahmad
, p. 20788 - 20793 (2021/07/01)
Oxidative dehydrogenative homo-coupling of amines to imines and cross-coupling of amines with alcohols to amides was achieved with high to moderate yields at room temperature in THF using Cu-MOF as an efficient and recyclable heterogeneous catalyst under mild conditions. Different primary benzyl amines and alcohols could be utilized for the synthesis of a wide variety of amides and imines. The Cu-MOF catalyst could be recycled and reused four times without loss of catalytic activity.
Iridium-Catalyzed Direct C-H Amidation Producing Multicolor Fluorescent Molecules Emitting Blue-to-Red Light and White Light
Hwang, Soon-Hyeok,Choi, Tae-Lim
, p. 2935 - 2940 (2020/04/20)
We report a powerful strategy, iridium-catalyzed direct C-H amidation (DCA) for synthesizing various fluorescent sulfonamides that emit light over the entire visible spectrum with excellent efficiency (up to 99% yields). By controlling electronic characters of the resulting sulfonamides, a wide range of blue-to-red emissions was predictably obtained via an excited-state intramolecular proton-transfer process. Furthermore, we even succeeded in a white-light generation, highlighting that this DCA is an excellent synthetic method to prepare a library of fluorophores.
Methyl-triflate-mediated dearylmethylation of: N -(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature
Peng, Hui,Ma, Jinhui,Luo, Wenkun,Zhang, Guangwen,Yin, Biaolin
supporting information, p. 2252 - 2256 (2019/05/17)
We have developed a protocol for the dearylmethylation of N-(arylmethyl)carboxamides under metal-free conditions in an aqueous medium at room temperature. This protocol involves methyl triflate-mediated successive C-C and C-N bond cleavages (retro-Mannich reaction) induced by electrophilic dearomatization/rearomatization. The dearomatization/rearomatization strategy can be expected to inspire the development of novel transformations based on the C-C bond cleavage in an environmentally benign manner.
Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines
Ghosh, Santanu,Jana, Chandan K.
, p. 260 - 266 (2018/02/19)
Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.
Nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source
Wen, Xue-Ping,Han, Yu-Ling,Chen, Jian-Xin
, p. 45107 - 45112 (2017/10/13)
The nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source is developed. The procedure can prepare both tertiary and secondary amides, and is applicable to various carbamoylsilanes and aryl halides containing differen
Synthesis of Secondary Aromatic Amides via Pd-Catalyzed Aminocarbonylation of Aryl Halides Using Carbamoylsilane as an Amide Source
Tong, Wenting,Cao, Pei,Liu, Yanhong,Chen, Jianxin
, p. 11603 - 11608 (2017/11/10)
Using N-methoxymethyl-N-organylcarbamoyl(trimethyl)silanes as secondary amides source, the direct transformation of aryl halides into the corresponding secondary aromatic amides via palladium-catalyzed aminocarbonylation is described. The reactions tolerated a broad range of functional groups on the aryl ring except big steric hindrance of substituent. The types and the relative position of substituents on the aryl ring impact the coupling efficiency.
Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides
Ghosh, Santanu,Jana, Chandan K.
supporting information, p. 5788 - 5791 (2016/11/29)
A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5′-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.
Covalent triazine framework-supported palladium as a ligand-free catalyst for the selective double carbonylation of aryl iodides under ambient pressure of CO
Wang, Zhifang,Liu, Cuibo,Huang, Yi,Hu, Yuchen,Zhang, Bin
supporting information, p. 2960 - 2963 (2016/02/19)
Carbonylation of aryl iodides with amines under atmospheric pressure of CO, catalyzed by Pd/CTFs (covalent triazine frameworks) without any specific additives, leads to the highly selective synthesis of α-ketoamides.
Direct oxidative amidation between methylarenes and amines in water
Wang, Tao,Yuan, Lin,Zhao, Zhenguang,Shao, Ailong,Gao, Meng,Huang, Yangfei,Xiong, Fei,Zhang, Huali,Zhao, Junfeng
supporting information, p. 2741 - 2744 (2015/05/27)
An environmentally friendly direct oxidative amidation between methylarenes and free amines was developed. The aromatic amide could be prepared efficiently from raw chemicals by employing TBHP as a "green" oxidant with co-catalysis of TBAI and FeCl3 in water.
Highly selective palladium-catalysed aminocarbonylation of aryl iodides using a bulky diphosphine ligand
De La Fuente, Veronica,Godard, Cyril,Claver, Carmen,Castillon, Sergio
experimental part, p. 1971 - 1979 (2012/09/22)
An efficient methodology for the synthesis of amides via palladium-catalysed aminocarbonylation of aryl iodides is reported using the bulky cis-1,2-bis[(di-tert-butylphosphino)methyl]cyclohexane ligand under atmospheric pressure of carbon monoxide. Excellent conversions (up to 99%) and chemoselectivities (up to 99%) were obtained for a range of aryl iodides and amine nucleophiles. The effect of the substituents on the substrate and nucleophiles on the catalytic performance was investigated. An NMR study was also carried out and key intermediates of the catalytic cycle were detected and characterised. Copyright
