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J Am Chem Soc. 2015 Mar 18;137(10):3490-3. doi: 10.1021/jacs.5b00939. Epub 2015 Mar 5.

Silver-catalyzed ring-opening strategy for the synthesis of β- and γ-fluorinated ketones.

Author information

1
†Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China.
2
‡Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China.

Abstract

A regioselective synthesis of β- and γ-fluorinated ketones via silver-catalyzed ring opening is described. A variety of β- and γ-fluorinated ketones are efficiently prepared, respectively, from tertiary cyclopropanol and cyclobutanol precursors, providing a straightforward approach for the introduction of a fluorine atom into complex molecules. Preliminary mechanistic studies suggest that a radical-mediated sequential C-C bond cleavage and C-F bond formation pathway is involved.

PMID:
25734528
DOI:
10.1021/jacs.5b00939

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