56753-75-4Relevant academic research and scientific papers
Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesviaN2H4mediated deoxygenative couplings
Lv, Leiyang,Li, Chao-Jun
, p. 2870 - 2875 (2021/03/14)
Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketonesviaN2H4mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.
A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters
Lima, Fabio,Sharma, Upendra K.,Grunenberg, Lars,Saha, Debasmita,Johannsen, Sandra,Sedelmeier, Joerg,Van der Eycken, Erik V.,Ley, Steven V.
supporting information, p. 15136 - 15140 (2017/11/20)
We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron-deficient olefins via radical addition to efficiently form C?C coupled products in a redox-neutral fashion. The Lewis base catalyst was shown to form a redox-active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.
Continuous UV-Flow Microsystem for Efficient Radical Generation from Organotrifluoroborates by Photoredox Catalysis
El Achi, Nassim,Penhoat, Ma?l,Bakkour, Youssef,Rolando, Christian,Chausset-Boissarie, La?titia
supporting information, p. 4284 - 4288 (2016/09/13)
An efficient continuous-flow protocol for C–O and C–C bond formation from organoborates by photoredox catalysis under UV irradiation was explored. The combination of a cyclometalated iridium photocatalyst, high-power UV light-emitting diode irradiation, and microreactor technology resulted in very efficient radical generation. The flow device enabled determination of highly accurate kinetic data that allowed the observation of good correlations with the standard Hammett σ (–0.26 to 0.227) values for a wide variety of substituents on the benzyl moiety (? = –4.70, R2= 0.98). Good to excellent yields were obtained for a variety of substrates by applying significantly short residence times.
Nickel-catalysed para-CH activation of pyridine with switchable regioselective hydroheteroarylation of allylarenes
Lee, Wei-Chih,Chen, Chien-Hung,Liu, Cheng-Yuan,Yu, Ming-Shiuan,Lin, Yung-Huei,Ong, Tiow-Gan
supporting information, p. 17104 - 17107 (2015/12/01)
para-CH activation of pyridine with allylbenzene is described by Ni/Al cooperative catalysis in combination with a bulkier NHC ligand and a Lewis acid, leading to linear hydroheteroarylation products. Interestingly, the branch selectivity can be achieved by using the combination of a less sterically hindered amino-NHC ligand and AlMe3 through tandem reaction of facile alkene isomerization followed by a slow CH bond activation process.
Intramolecular Alkylations of Aromatic Compounds, XVIII: Synthesis of 3,4-Dihydro-1'-methylspiro
Reimann, Eberhard,Speckbacher, Johann,Lotter, Hermann
, p. 385 - 393 (2007/10/02)
Refluxing the tetrahydroyridines 10 in hydrobromic acid gives the title compounds 12 stereoselectively.Their structures and configurations were confirmed by NMR spectroscopy and X-ray analysis.The tetrahydropyridines 10 were prepared from the pyridinecarbonitriles 5 and Grignard reagents 6 by standard methods.
Hypolipidemic alkenesulfonamides
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, (2008/06/13)
Method for lowering blood liped levels in mammals, using certain derivatives of N-carbamoyl-2-phenylethenesulfonamide, many of which are novel.
