Nickel-Catalyzed Enantioselective Arylative Activation of Aromatic C–O Bond

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2021-11, Vol.143 (44), p.18380-18387
Main Authors: Zhang, Jintong, Sun, Tingting, Zhang, Zishuo, Cao, Haiqun, Bai, Zhushuang, Cao, Zhi-Chao
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c09797