Effect of Brønsted acids on the thiophenol-mediated radical addition–translocation–cyclization process for the preparation of pyrrolidine derivatives Article Swipe
Related Concepts
Thiophenol
Chemistry
Pyrrolidine
Trifluoroacetic acid
Radical
Protonation
Brønsted–Lowry acid–base theory
Hydrogen atom
Alkyne
Radical cyclization
Amine gas treating
Sulfonamide
Combinatorial chemistry
Photochemistry
Medicinal chemistry
Organic chemistry
Catalysis
Group (periodic table)
Ion
Valentin Soulard
,
F. Dénès
,
Philippe Renaud
·
YOU?
·
· 2016
· Open Access
·
· DOI: https://doi.org/10.1080/10715762.2016.1223294
· OA: W2517686946
YOU?
·
· 2016
· Open Access
·
· DOI: https://doi.org/10.1080/10715762.2016.1223294
· OA: W2517686946
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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