345-71-1Relevant academic research and scientific papers
Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage
Ma, Yangmin,Shao, Lei,Szostak, Michal,Wang, Ruihong,Zhang, Jin,Zhang, Pei
supporting information, (2022/01/04)
Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe
Pd/C in Propylene Carbonate: A Sustainable Catalyst–Solvent System for the Carbonylative Suzuki–Miyaura Cross-Coupling Using N-Formylsaccharin as a CO Surrogate
Gautam, Prashant,Gupta, Rashi,Bhanage, Bhalchandra M.
, p. 3431 - 3437 (2017/07/04)
This work documents the first Pd/C-catalyzed carbonylative Suzuki–Miyaura cross-coupling of aryl iodides with N-formylsaccharin as a CO surrogate. In contrast to previous reaction protocols, which make use of toxic and hazardous solvents, the reaction could be advantageously performed in propylene carbonate as an environmentally benign and sustainable polar aprotic solvent. A range of biaryl ketones, including (4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone, an antineoplastic belonging to the phenstatin family, could be synthesized under cocatalyst-free, additive-free and ligand-free conditions. The Pd/C could be recycled up to five times under CO surrogacy with only a marginal decrease in catalytic activity. The reaction could also be scaled up to gram-scale syntheses.
A Rapid Injection NMR Study of the Reaction of Organolithium Reagents with Esters, Amides, and Ketones
Plessel, Kristin N.,Jones, Amanda C.,Wherritt, Daniel J.,Maksymowicz, Rebecca M.,Poweleit, Eric T.,Reich, Hans J.
, p. 2310 - 2313 (2015/05/27)
Unexpectedly high rates of reaction between alkyllithium reagents and amides, compared to esters and ketones, were observed by Rapid Inject NMR and competition experiments. Spectroscopic investigations with 4-fluorophenyllithium (ArLi, mixture of monomer and dimer in THF) and a benzoate ester identified two reactive intermediates, a homodimer of the tetrahedral intermediate, stable below -100°C, and a mixed dimer with ArLi. Direct formation of dimers suggested that the ArLi dimer may be the reactive aggregate rather than the usually more reactive monomer. In contrast, RINMR experiments with ketones demonstrated that the ArLi monomer was the reactive species. (Chemical Equation Presented).
Metal bis{(trifluoromethyl)sulfonyl}amide complexes: Highly efficient Friedel-Crafts acylation catalysts
Earle, Martyn J.,Hakala, Ullastiina,McAuley, Barry J.,Nieuwenhuyzen, Mark,Ramani, Alwar,Seddon, Kenneth R.
, p. 1368 - 1369 (2007/10/03)
A range of metal bis{(trifluoromethyl)sulfonyl}amide complexes, including many unreported ones, have been synthesised, most of which have been found to be excellent Friedel-Crafts acylation catalysts in the absence of solvent; these reactions have also been carried out in ionic liquids, which allow the catalysts to be recycled and reused.
Preparation process of fluorine substituted aromatic compound
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, (2008/06/13)
A preparation process of a fluorine substituted aromatic compound comprising reacting an alkali metal or alkali earth metal salt of an aromatic compound having a hydroxy group with an organic fluorinating agent is disclosed. As a representative fluorinating agent, a bis-dialkylamino-difluoromethane compound, for example, 2,2′-difluoro-1,3-dimethylimidazolidine, is exemplified. According to the process, an industrially useful fluorinated aromatic compound, for example, a fluorobenzene, a fluorine substituted benzophenone, a fluorine substituted diarylsulfone can be prepared with ease in economy without specific equipment.
