SelectfluorTM F-TEDA-BF4 as a Versatile Mediator or Catalyst in  Organic  Chemistry

 Stojan Stavbera* and Marko Zupana,b
a »Jožef Stefan« Institute, Jamova 39, 1000 Ljubljana, Slovenia, e-mail:
Department of Chemistry, Faculty for Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia

SelectfluorTM F-TEDA-BF4 1 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra-fluoroborate)) is not only one of the most valuable reagents for electrophilic fluorination but also a versatile mediator or catalyst for various other functionalisations of organic compounds. Its application for selective and effective iodination, bromination, chlorination, nitration and thiocyanation of a comprehensive range of organic compound is reviewed. Benzylic functionalisation of hexamethylbenzene mediated with F-TEDA-BF4 in the presence of various sources of nucleophiles is described and a method for the synthesis of para-quinols or para-quinol ethers emphasised. F-TEDA-BF4 is also useful for the promotion of allylstannation of aldehydes and imines, cleavage of p-methoxybenzylidene (PMP), tetrahydropyranyl (THP) or 1,3-dithiane protection, and rearrangements of bicyclic iodides, as well as for catalysis of the regioselective ring opening of epoxides or [4+2] cycloaddition reactions between imines and cyclic enol ethers.

Key words: SelectfluorTM F-TEDA-BF4, iodination, bromination, hexametylbenzene, allylstannation, deprotection