Effect of Brønsted acids on the thiophenol-mediated radical addition-translocation-cyclization process for the preparation of pyrrolidine derivatives.
Free Radic Res
; 50(sup1): S2-S5, 2016 Nov.
Article
em En
| MEDLINE
| ID: mdl-27684302
ABSTRACT
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.
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Base de dados:
MEDLINE
Assunto principal:
Fenóis
/
Pirrolidinas
/
Compostos de Sulfidrila
/
Radicais Livres
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article