General Method for the Suzuki–Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature
journal contribution
posted on 2017-11-27, 16:37 authored by Peng Lei, Guangrong Meng, Yun Ling, Jie An, Steven P. Nolan, Michal SzostakA 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.
