American Chemical Society
ol7b03191_si_001.pdf (4.81 MB)

General Method for the Suzuki–Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)­(cin)Cl] at Room Temperature

Download (4.81 MB)
journal contribution
posted on 2017-11-27, 16:37 authored by Peng Lei, Guangrong Meng, Yun Ling, Jie An, Steven P. Nolan, Michal Szostak
A general, highly selective method for the room temperature Suzuki–Miyaura cross-coupling of commonly encountered primary benzamides is reported. A combination of site-selective N,N-di-Boc-activation (tert-butoxycarbonyl activation) of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd­(NHC)­(cin)­Cl] (NHC = N-heterocyclic carbene; cin = cinnamyl) provides a highly effective route to biaryl ketones from primary amides in high yields. For the first time, a TON of >1000 has been achieved in amide acyl cross-coupling.