期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 11, 期 -, 页码 2737-2746出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.11.295
关键词
carbene ligand; C-H arylation; gold catalysis
资金
- ERATO program from JST
- MEXT [26810057, 23750038]
- JSPS
- World Premier International Research Center (WPI) Initiative (Japan)
- Grants-in-Aid for Scientific Research [23750038, 26810057] Funding Source: KAKEN
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.
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