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: stojan.stavber@ijs.si
b Department
of Chemistry, Faculty for Chemistry and Chemical Technology, University of
Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
Abstract:
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