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- Title
Site-Selective Approach to β-Fluorination: Photocatalyzed Ring Opening of Cyclopropanols.
- Authors
Bloom, Steven; Bume, Desta Doro; Pitts, Cody Ross; Lectka, Thomas
- Abstract
To expand upon the recent pioneering reports of catalyzed sp3 CH fluorination methods, the next rational step is to focus on directing 'radical-based fluorination' more effectively. One potential solution entails selective CC bond activation as a prelude to selective fluorination. Herein, we report the tandem photocatalyzed ring-opening/fluorination reactions of cyclopropanols by 1,2,4,5-tetracyanobenzene (TCB) and Selectfluor to afford a process tantamount to site-selective β-fluorination of carbonyl-containing compounds. This new approach provides a synthetically mild and operationally simple route to otherwise difficult-to-prepare β-fluorinated products in good yields and with good-to-excellent regioselectivity. Remarkably, substrates that contain other usually reactive (e.g., benzylic) sites undergo ring-opening fluorination preferably. The versatility of this method to give cyclic β-fluorides from tertiary cyclopropanols and γ-fluoro alcohols is also highlighted.
- Subjects
FLUORINATION; PHOTOCATALYSIS; CYCLOPROPANOL; CARBONYL compounds; FLUORIDES
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 22, p8060
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201501081