Copper-Catalyzed Asymmetric Hydroboration of Alkynes to C-N Axially Chiral Azaborines via Dynamic Kinetic Resolution.

Chengchao Guo, Chao Li, Xuzhao Du, Yiyun Pan, Kai Yang, Peiyuan Yu, Qiuling Song

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Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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7 authors.

Chengchao GuoKey Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources, Fuzhou University, Fuzhou, China.

Chao LiKey Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources, Fuzhou University, Fuzhou, China.

Xuzhao DuDepartment of Chemistry and Guangming Advanced Research Institute, Southern University of Science and Technology, Shenzhen, China.

Yiyun PanKey Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources, Fuzhou University, Fuzhou, China.

Kai YangKey Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources, Fuzhou University, Fuzhou, China.ORCID https://orcid.org/0000-0002-1495-5380

Peiyuan YuDepartment of Chemistry and Guangming Advanced Research Institute, Southern University of Science and Technology, Shenzhen, China.ORCID https://orcid.org/0000-0002-4367-6866

Qiuling SongKey Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources, Fuzhou University, Fuzhou, China.

Funding

Center for Computational Science and Engineering and the CHEM High-Performance Supercomputer Cluster (CHEM-HPC) of the Department of Chemistry, Southern University of Science and TechnologyHenan Normal UniversityHenan University DCSHENU2405National Key R&D Program of China 2023YFF0723900National Natural Science Foundation of China 22271048National Natural Science Foundation of China 22271105Open Research Fund of State Key Laboratory of Coordination ChemistrySchool of Chemistry and Chemical Engineering, Nanjing University and Open Research Fund of School of Chemistry and Chemical EngineeringShenzhen Science and Technology Program KQTD20210811090112004

6 · The paper itself

Abstract

Despite the substantial application potential of C-N axially chiral motifs across diverse fields, and the growing interest in azaborine frameworks owing to their distinctive physicochemical properties, the direct catalytic synthesis of C-N axially chiral azaborines has remained elusive, significantly impeding the practical deployment of these promising molecular scaffolds. Herein, we disclose a copper-catalyzed asymmetric hydroboration reaction of alkynes with N-arylazaborines under mild reaction conditions, which enables the efficient access to C-N axially chiral azaborine products in high yields, accompanied by excellent regioselectivity, Z-stereoselectivity, and enantioselectivity. Mechanistic experiments and density functional theory calculations reveal that a dynamic kinetic resolution process is involved in this reaction. Specifically, the two enantiomers of racemic N-arylazaborines can undergo racemization via a dearomative tetracoordinate boron intermediate under the action of NaO

Indexed as

asymmetric hydroborationazaborine ringC–N axial chiralitycopper catalysis

Identifiers

PMID42233515

DOI10.1002/anie.8039085

PMCPMC13360390

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