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Letter

Selective and Effective Fluorination of Organic Compounds in Water Using Selectfluor F-TEDA-BF₄

Supporting Info

Gaj Stavber,^† Marko Zupan,^†^‡ Marjan Jereb,^† and Stojan Stavber*^‡

Laboratory for Organic and Bioorganic Chemistry, Jozef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia, and Department of Chemistry of the Faculty for Chemistry and Chemical Technology, University of Ljubljana, Aker

eva 5, 1000 Ljubljana, Slovenia

Org. Lett., 2004, 6 (26), pp 4973–4976

DOI: 10.1021/ol047867c

Publication Date (Web): December 1, 2004

†

University of Ljubljana.

‡

“Jozef Stefan” Institute.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, stojan.stavber@ijs.si

Abstract

Selective and effective fluorination of various types of organic compounds performed in water as the reaction medium using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF₄) is reported. 2-Naphthole and 2-methoxynaphthalene were thus transformed to 1,1-difluoro-2(1H)naphthalenone, estrone to 10β-fluoro-1,4-estradien-3,17-dione, phenyl-substituted alkenes to vicinal fluorohydrins, and various ketones, 1,3-diketones, or β-ketoesters to corresponding α-fluoro or α,α-difluoro ketones.

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History

Published In Issue December 23, 2004
Received October 15, 2004

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Letter

Selective and Effective Fluorination of Organic Compounds in Water Using Selectfluor F-TEDA-BF₄