1696-17-9Relevant academic research and scientific papers
Aminocarbonylation reaction using palladium complexes containing phosphorus-nitrogen ligands as catalysts
Aranda,Zolezzi,Valdebenito,Cáceres-Vásquez,Moya,Aguirre
, p. 2136 - 2137 (2013)
The catalytic activities of palladium complexes containing phosphorus-nitrogen ligands is reported. The catalysts studied showed high activities in the aminocarbonylation of aryl iodides. The palladium complexes reported activities between 100% and 58% in the aminocarbonylation reaction. The reactions are very selective for the double carbonylative amination of aryl halides. The major product is N,N-diethyl-?-oxo benzeneacetamide (96/4). The reaction was made under mild conditions of temperature and carbon monoxide pressure.
Heck reactions of ortho-substituted arenediazonium salts: Critical observations on electronic effects
Sengupta, Saumitra,Bhattacharyya, Sanchita
, p. 2035 - 2037 (2001)
An attempted Heck reaction of o-diethylamido phenyldiazonium tetrafluoroborate follows a unique radical-chain protodediazoniation pathway that is triggered by a facile 1,5-[H] shift of the derived aryl radical. Other ortho-substituted salts, irrespective of their redox potentials and structure, behave in the normal way.
Bimetallic activation in homogeneous catalysis. Part II. Formation of α-oxo amide by palladium-catalyzed double carbonylation of the tricarbonyl (chlorobenzene) chromium complex
Dany, Fabienne,Mutin, Robert,Lucas, Christine,Dufaut, Veronique,Thivolle-Cazat, Jean,Basset, Jean Marie
, p. L15 - L20 (1989)
The authors report that tricarbonyl (chlorobenzene) chromium can undergo a double carbonylation in the presence of diethylamine to give the corresponding α-oxo amide. This is the first report of an easy access to the double carbonylation of chloroarene de
Safer solvents for reactive organometallic reagents
Malinski, Thomas J.,Bergbreiter, David E.
, p. 3926 - 3929 (2018)
This paper describes the use of poly(α -olefin)s (PAOs) as safer alternatives to cyclohexane, hexanes, and heptane as solvents for alkyllithium reagents. While PAOs like any alkane are flammable, PAOs do not readily catch on fire because they contain 20 or more carbon atoms, a low volatility, and have a high flash point vis-à-vis alkanes like hexane. Also unlike conventional alkanes, PAOs can be quantitatively separated from polar organic solvents and polar organic products either by a simple gravity separation or by an extraction after a reaction. Any leaching of the PAO solvent into a polar phase during such a separation can be minimized by addition of small amounts of water to the polar phase. However, while these PAO solvents have some physical differences from conventional low molecular weight volatile alkanes, they otherwise behave like alkanes and alkyllithium reagents in these PAO solvents can used in their conventional reactions in these PAO solvents.
The metal-halogen exchange reaction between ortho-substituted aryl halides and Ph2CuLi·LiCN: Scope and applicability for coupling reactions
?etin, Fatma,Bari? ?eno?ul,Gezer, Sibel,Astley, Demet,Astley, Stephen T.
, p. 154 - 157 (2004)
Metal-halogen exchange between Ph2CuLi · LiCN and ortho-substituted aryl iodides or bromides may be used to conveniently afford substituted metallated aryls which can subsequently undergo reaction with electrophiles.
An experimentalist's guide to electrosynthesis: The Shono oxidation
Alfonso-Súarez, Paulino,Kolliopoulos, Athanasios V.,Smith, Jamie P.,Banks, Craig E.,Jones, Alan M.
, p. 6863 - 6867 (2015)
Electrosynthesis is a powerful method to functionalise organic molecules without the need to use chemical reagents or protecting groups, yet it is not widely used in synthesis. In this study, we investigated the Shono oxidation of a tertiary amide (electrochemical functionalisation of a C-H bond adjacent to an amide nitrogen atom), demonstrating the value of performing cyclic voltammetry, varying voltage and charge per mole, selection of electrolyte and electrode material. We demystify the process to demonstrate a simple relationship between oxidation potential, and charge transfer required, which affords a high conversion to the desired alpha-methoxylated product using an undivided experimental cell.
Sustainable triazine-based dehydro-condensation agents for amide synthesis
Sole, Roberto,Gatto, Vanessa,Conca, Silvia,Bardella, Noemi,Morandini, Andrea,Beghetto, Valentina
, (2021)
Conventional methods employed today for the synthesis of amides often lack of economic and environmental sustainability. Triazine-derived quaternary ammonium salts, e.g., 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM(Cl)), emerged as promising dehydro-condensation agents for amide synthesis, although suffering of limited stability and high costs. In the present work, a simple protocol for the synthesis of amides mediated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a tert-amine has been described and data are compared to DMTMM(Cl) and other CDMT-derived quaternary ammonium salts (DMT-Ams(X), X: Cl? or ClO4?). Different tert-amines (Ams) were tested for the synthesis of various DMT-Ams(Cl), but only DMTMM(Cl) could be isolated and employed for dehydro-condensation reactions, while all CDMT/tert-amine systems tested were efficient as dehydro-condensation agents. Interestingly, in best reaction conditions, CDMT and 1,4-dimethylpiperazine gave N-phenethyl benzamide in 93% yield in 15 min, with up to half the amount of tert-amine consumption. The efficiency of CDMT/tert-amine was further compared to more stable triazine quaternary ammonium salts having a perchlorate counter anion (DMT-Ams(ClO4)). Overall CDMT/tert-amine systems appear to be a viable and more economical alternative to most dehydro-condensation agents employed today.
Oxidation of benzylamines to amides
Markgraf, J. Hodge,Sangani, Poorab K.,Finkelstein, Manuel
, p. 1285 - 1290 (1997)
A convenient method for the conversion of tertiary benzylamines to benzamides by phase transfer oxidation is described. Yields are good. Regioselectivities are reported.
TBAI-catalyzed C–N bond formation through oxidative coupling of benzyl bromides with amines: a new avenue to the synthesis of amides
Kumar, Dhirendra,Maury, Suresh Kumar,Kumari, Savita,Kamal, Arsala,Singh, Himanshu Kumar,Singh, Sundaram,Srivastava, Vandana
supporting information, p. 424 - 432 (2022/02/09)
A new green approach for the synthesis of amide through TBAI-catalyzed oxidative coupling of benzyl bromides with amine was developed in the presence of tert-butyl hydroperoxide (TBHP) as an oxidant. Various electron-donating and withdrawing groups containing benzyl bromides and various amines, were subjected to the reaction and transformed to the corresponding amide in good to excellent yields.
One-pot synthesis of a highly disperse core-shell CuO-alginate nanocomposite and the investigation of its antibacterial and catalytic properties
Habibi, Hassan,Mansourinejhad, Sanam,Saberi, Dariush,Shadi, Ahmad
, p. 199 - 211 (2021/12/30)
In this study, sodium alginate was extracted from Sargassum algae, collected from coastal waters of Bushehr, Persian Gulf, Iran and used as a stabilizing and wrapping agent for CuO nanoparticles. The synthesized nanocomposite was characterized by some spectroscopic and microscopic techniques, such as IR, XRD, Uv-vis, BET, BJH, zeta potential, SEM, TEM, HR-TEM, and XPS. The antibacterial effects of the CuO-alginate nanocomposite against some bacteria, isolated from a burn wound, were evaluated. The results showed that this nanocomposite had better antibacterial effects than its components onPseudomonas aeruginosaATCC 27853,Staphylococcus aureusATCC 12600,Streptococcus pyogenesATCC 19615, andStaphylococcus epidermidisATCC 49461. Among these,Staphylococcus aureusATCC 12600 was the most sensitive one to this nanocomposite, with the lowest minimum inhibitory concentration (2.08 mg mL?1) observed. Moreover, the synthesized nanocomposite showed good catalytic activity in the oxidative coupling of carboxylic acids withN,N-dialkylformamides toward the synthesis of amides.
