Effect of Brønsted acids on the thiophenol-mediated radical addition–translocation–cyclization process for the preparation of pyrrolidine derivatives

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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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)

Division/Institute:

08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Soulard, Valentin Emmanuel; Dénès, Fabrice Pierre François and 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:

24 Jun 2021 11:19

Publisher DOI:

10.1080/10715762.2016.1223294

BORIS DOI:

10.48350/157105

URI:

https://boris.unibe.ch/id/eprint/157105

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