期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 22, 页码 8060-8063出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501081
关键词
CC activation; cyclopropanols; fluorination; photochemistry; radical ions
资金
- NSF [CHE 1152996]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1152996] Funding Source: National Science Foundation
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 -fluorination of carbonyl-containing compounds. This new approach provides a synthetically mild and operationally simple route to otherwise difficult-to-prepare -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 -fluorides from tertiary cyclopropanols and -fluoro alcohols is also highlighted.
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