Magnesium-mediated arylation of amines via C-F bond activation of fluoroarenes
A series of new Mg(ii) amides featuring a bulky β-diketiminate backstop ligand, has been synthesised. These complexes are demonstrated to be excellent sources of nucleophilic amides that can participate in rapid C-F activation of several fluoroarenes at room temperature or using microwave assistance, leading to the installment of synthetically important C-N bonds via nucleophilic substitution.
Bole, Leonie J.,Davin, Laia,Kennedy, Alan R.,McLellan, Ross,Hevia, Eva
supporting information
p. 4339 - 4342
(2019/04/26)
Microwave-promoted piperidination of halopyridines: A comparison between Ullmann, Buchwald-Hartwig and uncatalysed SNAr reactions
A comparative study between the most used methodologies for the preparation of piperidinyl pyridines (Buchwald-Hartwig reaction, Ullmann reaction and nucleophilic aromatic substitution (SNAr)) by microwave-assisted piperidination of halopyridines is reported. Our results suggest that the Ullmann reaction is most effective for less reactive halopyridines, while uncatalysed SNAr is sufficient for more reactive ones. Copyright
Yaunner, Ricardo S.,Barros, Jose C.,Da Silva, Joaquim F. M.
experimental part
p. 273 - 276
(2012/09/21)
Direct uncatalyzed amination of 2-chloropyridine using a flow reactor
Chloropyridines are efficiently converted into 2-amino-pyridines by uncatalyzed nucleophilic aromatic substitution (SNAr) in NMP using a continuous-flow reactor. A variety of secondary amines undergo SNAr with both electron-rich and electron-deficient 2-chloropyridines to afford 2-aminopyridines in good to excellent yield. The flow reactor, which provides a short reaction time and high temperatures up to 300°C, can overcome the activation barrier for reactions with unactivated substrates. Short reaction times result in fewer side products and can afford milligram to multigram quantities of product using continuous flow. Georg Thieme Verlag Stuttgart.
Hamper, Bruce C.,Tesfu, Eden
p. 2257 - 2261
(2008/02/10)
STUDIES ON HETEROCYCLIC QUATERNARY NITROGEN BASES: KINETICS OF TRANSALKYLATION OF PRIMARY AMINES BY N-SUBSTITUTED 5,6-DIHYDRO-2,4-DIPHENYLNAPHTHOPYRIDINIUM CATIONS
N-substituents in 5,6-dihydro-2,4-diphenylnaphthopyridiniums are transferred to piperidine by unimolecular and / or bimolecular processes in chlorobenzene solution.The kinetics of this reaction at variable temperatures were studied.It has been shown that the reaction follows either SN1 or SN2 mechanisms dependant on the nature of N-substituent.
Elshafie, Sayed Mahmoud M.
p. 525 - 528
(2007/10/02)
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