333349-88-5Relevant academic research and scientific papers
Radical-mediated divergent cyclization of benzamides toward perfluorinated or cyanated isoquinolinediones
Deng, You-Lin,Tang, Shi,Ding, Guo-Liang,Wang, Ming-Wei,Li, Jie,Li, Zeng-Zeng,Yuan, Li,Sheng, Rui-Long
, p. 9348 - 9353 (2016)
A simple and efficient copper-controlled divergent cyclization of benzamides, which leads to perfluorinated or cyanated isoquinolinediones, is developed. In the presence of AIBN, methacryloyl benzamides with perfluoroalkyl iodides undergo cascade radical addition/cyclization to afford perfluoroinated isoquinolinediones as the major product under metal-free conditions, whereas the use of CuI (10 mol%) is able to redirect the cyclization to yield isoquinolinediones bearing an α-cyano quaternary carbon center. The cyclization features controllable divergent synthesis and a broad substrate scope as well as highly practical reaction conditions, thereby making this strategy a highly attractive means to fluorinate or cyanate isoquinolinediones.
Metal free amide synthesis via carbon-carbon bond cleavage
Zhu, Chunyin,Wei, Wei,Du, Peng,Wan, Xiaobing
, p. 9615 - 9620 (2015/01/09)
A metal-free oxidative coupling of methyl ketones and primary amines to amides has been developed. The reaction tolerates a variety of functional groups, and is operationally simple. The reaction is proposed to go through a radical pathway to form the triiodomethyl ketone intermediate and the amide is formed by the nucleophilic attack of amine on triiodomethyl ketone carbonyl.
A phosphine-free Pd catalyst for the selective double carbonylation of aryl iodides
De La Fuente, Veronica,Godard, Cyril,Zangrando, Ennio,Claver, Carmen,Castillon, Sergio
supporting information; experimental part, p. 1695 - 1697 (2012/03/22)
The first phosphine-free Pd-catalysed double carbonylation of aryl iodides is reported as a general and practical method, giving excellent conversions and selectivities for a wide range of aryl iodides and amine nucleophiles under atmospheric CO pressure. The Royal Society of Chemistry 2012.
Aminocarbonylations employing Mo(CO)6 and a bridged two-vial system: Allowing the use of nitro group substituted aryl iodides and aryl bromides
Nordeman, Patrik,Odell, Luke R.,Larhed, Mats
, p. 11393 - 11398 (2013/02/23)
A bridged two-vial system aminocarbonylation protocol where Mo(CO) 6 functions as an external in situ solid source of CO has been developed. For the first time both nitro group containing aryl/heteroaryl iodides and bromides gave good to excellent yields in the Mo(CO) 6-mediated and palladium(0)-catalyzed conversion to benzamides, while the identical one-vessel protocol afforded extensive reduction of the nitro functionality. The above-mentioned bridged two-compartment protocol furnished good results with both primary amines and secondary amines and sluggish aniline nucleophiles at 65-85 C reaction temperatures.
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
