Pyridylidene ligand facilitates gold-catalyzed oxidative C–H arylation of heterocycles

Beilstein Journal of Organic Chemistry

Hideto Ito¹  Kenichiro Itami¹  Kazuhiro Hata¹  Yasutomo Segawa¹ 

[1] Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan;

关键词: carbene ligand;    C–H arylation;    gold catalysis;   

DOI  :  10.3762/bjoc.11.295

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown