biostudies-literatureUnknown11Hata KTriaryl-2-pyridylidene effectively facilitates the gold-catalyzed oxidative C-H arylation of heteroarenes with arylsilanes as a unique electron-donating ligand on gold. The employment of the 2-pyridylidene ligand, which is one of the strongest electron-donating N-heterocyclic carbenes, resulted in the rate acceleration of the C-H arylation reaction of heterocycles over conventional ligands such as triphenylphosphine and a classical N-heterocyclic carbene. In situ observation and isolation of the 2-pyridylidene-gold(III) species, as well as a DFT study, indicated unusual stability of gold(III) species stabilized by strong electron donation from the 2-pyridylidene ligand. Thus, the gold(I)-to-gold(III) oxidation process is thought to be facilitated by the highly electron-donating 2-pyridylidene ligand.Beilstein journal of organic chemistry2737-46https://www.ebi.ac.uk/biostudies/studies/S-EPMC4734412biostudies-literaturePyridylidene ligand facilitates gold-catalyzed oxidative C-H arylation of heterocycles.PMC4734412Ito HSegawa YHata KItami KfalsePyridylidene ligand facilitates gold-catalyzed oxidative C-H arylation of heterocycles.Triaryl-2-pyridylidene effectively facilitates the gold-catalyzed oxidative C-H arylation of heteroarenes with arylsilanes as a unique electron-donating ligand on gold. The employment of the 2-pyridylidene ligand, which is one of the strongest electron-donating N-heterocyclic carbenes, resulted in the rate acceleration of the C-H arylation reaction of heterocycles over conventional ligands such as triphenylphosphine and a classical N-heterocyclic carbene. In situ observation and isolation of the 2-pyridylidene-gold(III) species, as well as a DFT study, indicated unusual stability of gold(III) species stabilized by strong electron donation from the 2-pyridylidene ligand. Thus, the gold(I)-to-gold(III) oxidation process is thought to be facilitated by the highly electron-donating 2-pyridylidene ligand.2015-01-01T00:00:00Z20152026-05-05T07:13:42.941Z2019-03-27T02:07:57ZS-EPMC47344122687779610.3762/bjoc.11.295