jo201437j_si_001.pdf (350.44 kB)
Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions
journal contribution
posted on 2011-11-18, 00:00 authored by Kai Cheng, Chen Wang, Yiyuan Ding, Qingbao Song, Chenze Qi, Xian-Man ZhangPalladium 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.