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

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...

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Bibliographic Details
Published in:Organic letters 2004-12, Vol.6 (26), p.4973-4976
Main Authors: Stavber, Gaj, Zupan, Marko, Jereb, Marjan, Stavber, Stojan
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol047867c