Issue 1, 2014

Transition-metal-free, room-temperature radical azidofluorination of unactivated alkenes in aqueous solution

Abstract

We report herein the transition-metal-free azidofluorination of unactivated alkenes. Thus, the condensation of various alkenes with TMSN3 and Selectfluor in aqueous CH3CN at RT led to the efficient and regioselective synthesis of β-fluorinated alkyl azides with excellent functional group compatibility and good stereoselectivity. A single electron transfer mechanism involving the oxidative generation of azidyl radicals is proposed.

Graphical abstract: Transition-metal-free, room-temperature radical azidofluorination of unactivated alkenes in aqueous solution

Supplementary files

Article information

Article type
Research Article
Submitted
14 Nov 2013
Accepted
25 Nov 2013
First published
20 Dez 2013

Org. Chem. Front., 2014,1, 100-104

Transition-metal-free, room-temperature radical azidofluorination of unactivated alkenes in aqueous solution

Z. Li, C. Zhang, L. Zhu, C. Liu and C. Li, Org. Chem. Front., 2014, 1, 100 DOI: 10.1039/C3QO00037K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements