Premium
Suzuki Cross‐Coupling for Post‐Complexation Derivatization of Non‐Racemic Bis‐Cyclometalated Iridium(III) Complexes
Author(s) -
Mietke Thomas,
Cruchter Thomas,
Winterling Erik,
Tripp Matthias,
Harms Klaus,
Meggers Eric
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701758
Subject(s) - iridium , diastereomer , chemistry , benzothiazole , trifluoromethanesulfonate , derivatization , combinatorial chemistry , benzoxazole , suzuki reaction , stereocenter , enantiomer , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , high performance liquid chromatography , palladium
A straightforward method for post‐complexation derivatizations of diastereo‐ and enantiomerically pure bis‐cyclometalated benzoxazole and benzothiazole iridium(III) complexes is reported. Triflate‐ and bromine‐functionalized iridium(III) complex dimers, represented as [Ir(μ‐Cl)(C^N) 2 ] 2 , were converted to the corresponding diastereomeric complexes, represented as Ir(C^N) 2 (N^O), using readily available chiral salicyloxazolines and salicylthiazolines as ancillary ligands, which are represented as N^O. The Ir(C^N) 2 (N^O) complexes, formed as mixtures of diastereomers, were then resolved by flash chromatography and the diastereomerically pure complexes Ir(C^N) 2 (N^O) subjected to Suzuki cross‐couplings. The post‐complexation cross‐couplings proceed without affecting the metal‐located stereocenter and hence provide post‐complexation derivatized non‐racemic iridium(III) complexes, which were not easily accessible with previous methods. This strategy expands the toolbox to access functionalized non‐racemic iridium(III) complexes for diverse applications in the life sciences, materials sciences, and catalysis.