Harnessing the Lewis Acidity of HFIP through its Cooperation with a Calcium(II) Salt: Application to the Aza-Piancatelli Reaction
| Autor: | Bastien Michelet, Vincent Gandon, David Lebœuf, Emmanuelle Schulz, Alejandro Perez-Luna, Lucile Marin, Régis Guillot |
|---|---|
| Přispěvatelé: | Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Réactivité organométallique et catalyse pour la synthèse (ROCS), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Organic Chemistry Salt (chemistry) chemistry.chemical_element Alcohol General Chemistry Calcium 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Solvent chemistry.chemical_compound Yield (chemistry) [CHIM]Chemical Sciences Molecule Organic chemistry Lewis acids and bases ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Chemistry-A European Journal Chemistry-A European Journal, Wiley-VCH Verlag, 2016, 22 (45), pp.16165--16171. ⟨10.1002/chem.201603592⟩ Chemistry-A European Journal, 2016, 22 (45), pp.16165--16171. ⟨10.1002/chem.201603592⟩ Chemistry-A European Journal, Wiley-VCH Verlag, 2016, 22 (45), pp.16165-16171. ⟨10.1002/chem.201603592⟩ |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | A method to extend the scope of the aza-Piancatelli reaction between 2-furylcarbinols and anilines is depicted. We found that 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) is the solvent of choice for this transformation, as it outcompetes the usual solvents in terms of rate and yield. Side reactions and other issues raised by the title reaction are prevented, thereby providing an avenue to complex molecules that were previously inaccessible. Lewis acidity studies and computations were carried out to unveil the role of HFIP. Based on these results, we propose that HFIP is, in fact, acting as a Lewis acid and that its acidity can be enhanced when combined with a calcium(II) salt. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|