Enantio- and Regioselective Ni-Catalyzed Hydroarylation of Alkenes and Alkynes to Form C-N Axially Chiral Heterobiaryls.

Authors

Zhenyu Gou, Shuai Zhu, Binyang Jiang, Shi-Liang Shi

Published in

Journal of the American Chemical Society. Oct 01, 2026. Epub Oct 01, 2026.

Abstract

C-N axially chiral heterobiaryls are highly valuable yet synthetically challenging scaffolds. Atroposelective hydroarylation represents an ideal strategy for their construction, offering both high step- and atom-economy. Herein, we report an enantio- and regioselective Ni-catalyzed hydroarylation of unactivated alkenes for the efficient synthesis of C-N axially chiral heterobiaryls. The sterically demanding chiral N-heterocyclic carbene (NHC) ligands enable excellent control over regioselectivity and enantioselectivity, affording a broad range of axially chiral products in good to excellent yields with up to 98% ee. The reaction exhibits broad substrate scope and high functional-group tolerance. Furthermore, the catalytic strategy could be extended to the atroposelective hydroarylation of alkynes, providing direct access to axially chiral alkenyl heterobiaryls with excellent chemo-, regio-, enantio- and E/Z-selectivity. Notably, the use of MeONa proved crucial for precise control of alkene geometry. This study provides a robust platform to advance the development of atroposelective hydroarylation reactions, enabling the construction of a series of novel C-N axially chiral scaffolds.

PMID:
42832399
Bibliographic data and abstract were imported from PubMed on 06 Oct 2026.

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