N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions

Author:

Kitamura Tsugio1ORCID,Kitamura Daichi1,Oyamada Juzo1,Higashi Masahiro2,Kishikawa Yosuke2

Affiliation:

1. Department of Chemistry and Applied Chemistry Saga University Honjo-machi, Saga 840-8502 Japan

2. Daikin Industries, Ltd. Settsu Osaka 566-8585 Japan

Abstract

AbstractA new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alkanes, geminal difluorinated compounds, 2‐fluorinated‐1,3‐dicarbonyl compounds in good to high yields, respectively. This is a useful fluorination reaction that not only improves the issues of the fluorination reaction using conventional mCPBA as a terminal oxidant but also constructs a simpler catalytic cycle. The present N−F reagent can be recovered as 2,2’‐bipyridine.

Publisher

Wiley

Subject

General Chemistry

Reference40 articles.

1.  

2. G. A. Olah R. D. Chambers G. K. S. Prakash Synthetic Fluorine Chemistry John Wiley New York 1992;

3. M. Hudlicky A. E. Pavlath Chemistry of Organic Fluorine Compounds II American Chemical Society Washington DC 1995;

4. R. D. Chambers Fluorine in Organic Chemistry Blackwell Publishing Oxford 2004;

5. Recent Advances in Catalytic Enantioselective Fluorination Reactions

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