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N-Fluoro-1,4-Diazoniabicyclo[2.2.2]octane Dication Salts; Efficient Fluorinating Agents and Functionalization Mediators for Organic Compounds

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Abstract:

Fluorination of organic compounds using the most representative reagents from the group of N-fluoro-1,4-diazoniabicyclo[2.2.2]octane dication salts is reviewed. Data dealing with selective fluorofunctionalization of aromatics, alkenes, alkynes, saturated hydrocarbons, organometallics, and organic molecules bearing nitrogen, sulfur, phosphorus, silicon or carbonyl containing functional groups with Selectfluor™ F-TEDA-BF4 1 (1-chloromethyl- 4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra-fluoroborate)), Accufluor™ NFTh 2 (1-fluoro-4-hydroxy-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate)) or bis(NF)-TEDA-BF4 3 (1,4-difluoro-1,4-diazoniabicyclo[ 2.2.2]octane bis (tetrafluoroborate)) are systematically collected and comparatively evaluated. Fluorination of potentially bioactive organic molecules (steroids, pyrimidine bases, glycols ...) with the above mentioned reagents is particularly emphasized. Functionalization of organic compounds mediated by Selectfluor™ F-TEDA-BF4 is briefly reviewed.





Keywords: Fluorofunctionalization; Lewis acid; Markovnikov-type fluoro-methoxy adducts; anti-fluoromethoxylation; diastereoselectivity; dibenzofuran; electron transfer (ET); hexamethylbenzene; steric effects

Document Type: Research Article

Affiliations: Laboratory for Organic and Bioorganic Chemistry, Jozef Stefan, Institute, Jamova 39, 1000 Ljubljana, Slovenia.

Publication date: January 1, 2006

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