1008119-09-2Relevant articles and documents
Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones
Titze, Marvin,Heitk?mper, Juliane,Junge, Thorsten,K?stner, Johannes,Peters, René
, p. 5544 - 5553 (2021)
Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.
Palladium-catalyzed carbon-monoxide-free aminocarbonylation of aryl halides using N-substituted formamides as an amide source
Sawant, Dinesh N.,Wagh, Yogesh S.,Bhatte, Kushal D.,Bhanage, Bhalchandra M.
, p. 5489 - 5494 (2011)
A carbon-monoxide-free aminocarbonylation of various N-substituted formamides with aryl iodides and aryl bromides using palladium acetate and Xantphos is described. The developed methodology is applicable for a wide range of formamides and aryl halides containing different functional groups furnishing good to excellent yield of the corresponding products. N-substituted formamides are used as an amide source wherein a Vilsmeier-type intermediate plays a major role, thus eliminating the need of toxic carbon monoxide gas.
Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals
Hirata, Shuichi,Osako, Takao,Uozumi, Yasuhiro
, (2021/10/05)
We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.
NOVEL GPR119 AGONIST COMPOUNDS
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, (2017/10/26)
The present invention relates to novel compounds of formula (I), process for preparation of the same and composition comprising these compounds.
Copper-catalyzed amide bond formation from formamides and carboxylic acids
Liu, Hong-Qiang,Liu, Jun,Zhang, Yang-Hui,Shao, Chang-Dong,Yu, Jing-Xun
, p. 11 - 14 (2015/01/30)
A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.
A novel method for the conversion of carboxylic acids to N,N-dimethylamides using N,N-dimethylacetamide as a dimethylamine source
Aavula, Sanjeev Kumar,Chikkulapally, Anil,Hanumanthappa,Jyothi, Indira,Vinod,Sulur, Kumar,Manjunatha,Sythana, Suresh Kumar
, p. 155 - 159 (2013/07/11)
A simple, cost effective and environmentally benign method is reported for the preparation of N,N-dimethylamides from carboxylic acids. The versatility of the method is determined by synthesising a large number of N,N-dimethylamide derivatives. Carboxylic acids are heated at 160-165°C in N,N-dimethylacetamide solvent in the presence of1,1'-carbonyldiimidazole to afford the corresponding N,N-dimethylamides in good to excellent yields.
Sulfonylamidation of alkylbenzenes at benzylic position with p-toluenesulfonamide and 1,3-diiodo-5,5-dimethylhydantoin
Baba, Haruka,Togo, Hideo
experimental part, p. 2063 - 2066 (2010/06/19)
Treatment of alkylbenzenes with p-toluenesulfonamide and 1,3-diiodo-5,5-dimethylhydantoin (DIH) in a small amount of carbon tetrachloride at 60 °C gave the corresponding α-p-toluenesulfonylamido)alkylbenzenes in good to moderate yields. The present reaction is a simple method for the α-sulfonylamidation of the benzylic position in alkylbenzenes.
FUSED HETEROARYL MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-KB ACTIVITY AND USE THEREOF
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Page/Page column 83, (2009/10/09)
Novel non-steroidal compounds are provided which are useful in treating diseases or disorders associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity, including metabolic and inflammatory and immune diseases or disorders, ha
Therapeutic Compounds
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Page/Page column 52, (2010/11/28)
The invention provides a compound of formula I: wherein R1-R6, X, Y, and B have any of the values described herein, as well as salts of such compounds, compositions comprising such compounds, and therapeutic methods that comprise the administration of such compounds. The compounds are inhibitors of MAO-B enzyme function and are useful for improving cognitive function and for treating psychiatric disorders in animals.