American Chemical Society
Browse
jo201437j_si_001.pdf (350.44 kB)

Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions

Download (350.44 kB)
journal contribution
posted on 2011-11-18, 00:00 authored by Kai Cheng, Chen Wang, Yiyuan Ding, Qingbao Song, Chenze Qi, Xian-Man Zhang
Palladium acetate [Pd­(OAc)2]-catalyzed Hiyama cross-coupling of arenediazonium salts with organosilanes was found to generate biaryl products in high yields in alcoholic solutions. The simple and efficient protocol does not require any bases, ligands, or air/moisture. The transformation can tolerate either electron-donating or electron-withdrawing functional groups. Theoretical studies show that the transmetalation is the rate-limiting step for the cross-coupling reaction and both acetate and tetrafluoroborate anions may be involved in the direct reaction with the silicon atom.

History