Cu-catalyzed fluorination of diaryliodonium salts with KF.
A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a Cu(I)/Cu(III) catalytic cycle.
Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States, and School of Chemistry, University of Tasmania , Private Bag 75, Hobart, Tasmania 7001, Australia.
Naoko
N
Ichiishi
Allan J
AJ
Canty
Brian F
BF
Yates
Melanie S
MS
Sanford
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D054879:Halogenation; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D011789:Quantum Theory; D012492:Salts / Q000737:chemistry*
D009861:Onium Compounds; D012492:Salts; D003300:Copper; D007455:Iodine