Selective functionalization of imidazoles via an iodine-copper exchange reaction.
The reaction of protected 4,5-diiodoimidazoles with (PhMe2CCH2)2CuLi regioselectively provides 5-cuprated imidazoles, which readily react with various electrophiles furnishing functionalized imidazoles in good yields; remarkably, these resulting mono-iodoimidazoles undergo again an iodine-copper exchange reaction in the presence of sensitive functional groups, like an aldehyde or a ketone.
Yang
Xiaoyin
X
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5-13, Haus F, D-81377, München, Germany.
Knochel
Paul
P
D003300:Copper / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*
D007093:Imidazoles; D003300:Copper; D007455:Iodine