Nickel-Catalyzed Atroposelective Synthesis of Axially Chiral Heterobiaryls via De Novo Benzene Formation
Abstract
Axially chiral 1-aryl isoquinolines and their congeners have emerged as powerful ligands and organocatalysts in asymmetric catalysis. Herein, relying on enantio- and regioselective nickel-catalyzed reductive [2+4] annulation between heteroaryl-substituted alkynes and C(sp 2 )-type bis-electrophiles, we apply the general strategy of cross-electrophile de novo benzene formation in the highly atroposelective synthesis of diverse axially chiral heterobiaryls bearing isoquinoline, pyridine, pyrazine, or quinazoline substructure. Notably, high diastereoselectivities are also achieved in the case of the heterobiaryls containing two chiral axes. The synthetic utility of this method is exhibited by a variety of expedient downstream derivatizations.
Fields of Study & Subjects
Axial and Atropisomeric Chirality Synthesis
Asymmetric Synthesis and Catalysis
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 3
- Pages
- 1078–1083
- Publication date
- 13 January 2026
- Language
- EN