Effect of Brønsted acids on the thiophenol-mediated radical addition-translocation-cyclization process for the preparation of pyrrolidine derivatives
| Autor: | Valentin Soulard, Philippe Renaud, Fabrice Dénès |
|---|---|
| Přispěvatelé: | Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Microsystems Laboratory 4 (LMIS4), Ecole Polytechnique Fédérale de Lausanne (EPFL) |
| Rok vydání: | 2016 |
| Předmět: |
Pyrrolidines
Tertiary amine Free Radicals Radical Alkyne Protonation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Pyrrolidine chemistry.chemical_compound Cascade reaction Phenols 540 Chemistry Trifluoroacetic acid [CHIM]Chemical Sciences Organic chemistry Sulfhydryl Compounds chemistry.chemical_classification 010405 organic chemistry Thiophenol General Medicine 0104 chemical sciences chemistry Cyclization 570 Life sciences biology |
| Zdroj: | Soulard, Valentin; Dénès, Fabrice; Renaud, Philippe (2016). Effect of Brønsted acids on the thiophenol-mediated radical addition–translocation–cyclization process for the preparation of pyrrolidine derivatives. Free radical research, 50(S1), S2-S5. Taylor & Francis 10.1080/10715762.2016.1223294 Free Radical Research Free Radical Research, 2016, 50 (1), pp.S2-S5. ⟨10.1080/10715762.2016.1223294⟩ |
| ISSN: | 1029-2470 |
| DOI: | 10.1080/10715762.2016.1223294 |
| Popis: | A thiophenol-mediated method for the conversion of propargylamines to pyrrolidines under acidic conditions is described. This cascade reaction involves addition of a thiyl radical to the terminal alkyne followed by a 1,5-hydrogen transfer (radical translocation) and a rapid cyclization affording the pyrrolidine ring. Our studies reveal that complete protonation of the tertiary amine with 10 equivalents of trifluoroacetic acid avoids undesired hydrogen atom abstractions by the thiyl radicals. |
| Databáze: | OpenAIRE |
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