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Site‐Selective Approach to β‐Fluorination: Photocatalyzed Ring Opening of Cyclopropanols
Author(s) -
Bloom Steven,
Bume Desta Doro,
Pitts Cody Ross,
Lectka Thomas
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501081
Subject(s) - selectfluor , regioselectivity , chemistry , ring (chemistry) , tandem , halogenation , combinatorial chemistry , catalysis , organic chemistry , materials science , composite material
To expand upon the recent pioneering reports of catalyzed sp 3 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.