posted on 2021-10-27, 18:44authored byJintong Zhang, Tingting Sun, Zishuo Zhang, Haiqun Cao, Zhushuang Bai, Zhi-Chao Cao
The
pioneering nickel-catalyzed cross-coupling of C–O electrophiles
was unlocked by Wenkert in the 1970s; however, the transition-metal-catalyzed
asymmetric activation of aromatic C–O bonds has never been
reported. Herein the first enantioselective activation of an aromatic
C–O bond is demonstrated via the catalytic arylative ring-opening
cross-coupling of diarylfurans. This transformation is facilitated
via nickel catalysis in the presence of chiral N-heterocyclic
carbene ligands, and chiral 2-aryl-2′-hydroxy-1,1′-binaphthyl
(ArOBIN) skeletons are delivered axially in high yields with high
ee. Moreover, this versatile skeleton can be transformed into various
synthetic useful intermediates, chiral catalysts, and ligands by using
the CH- and OH-based modifiable sites. This chemistry features mild
conditions and good atom economy.