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
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Effect_of_Bronsted_acids_on_the_thiophenol_mediated_radical_addition_translocation_cyclization_process_for_the_preparation_of_pyrrolidine_derivatives.pdf - Published Version Available under License Creative Commons: Attribution-Noncommercial-No Derivative Works (CC-BY-NC-ND). Download (1MB) | Preview |
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.
Item Type: |
Journal Article (Original Article) |
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Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Soulard, Valentin Emmanuel, Dénès, Fabrice Pierre François, Renaud, Philippe |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1071-5762 |
Publisher: |
Taylor & Francis |
Language: |
English |
Submitter: |
Franziska Bornhauser-Rufer |
Date Deposited: |
24 Jun 2021 11:11 |
Last Modified: |
05 Dec 2022 15:51 |
Publisher DOI: |
10.1080/10715762.2016.1223294 |
BORIS DOI: |
10.48350/157105 |
URI: |
https://boris.unibe.ch/id/eprint/157105 |
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