{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["11"],"submitter":["Hata K"],"pubmed_abstract":["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."],"journal":["Beilstein journal of organic chemistry"],"pagination":["2737-46"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4734412"],"repository":["biostudies-literature"],"pubmed_title":["Pyridylidene ligand facilitates gold-catalyzed oxidative C-H arylation of heterocycles."],"pmcid":["PMC4734412"],"pubmed_authors":["Ito H","Segawa Y","Hata K","Itami K"],"additional_accession":[]},"is_claimable":false,"name":"Pyridylidene ligand facilitates gold-catalyzed oxidative C-H arylation of heterocycles.","description":"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.","dates":{"release":"2015-01-01T00:00:00Z","publication":"2015","modification":"2026-05-05T07:13:42.941Z","creation":"2019-03-27T02:07:57Z"},"accession":"S-EPMC4734412","cross_references":{"pubmed":["26877796"],"doi":["10.3762/bjoc.11.295"]}}