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DOI: 10.1055/a-2814-1218
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Synthesis of Chiral Boronated 1,4-cis-Cyclohexenes via Ni-Catalyzed Enantioselective Arylboration

Authors

  • Yunya Gu

    1   Fujian Province University, Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fuzhou, P. R. China (Ringgold ID: RIN12423)

  • Shanshan Cheng

    1   Fujian Province University, Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fuzhou, P. R. China (Ringgold ID: RIN12423)

  • Yanping Zheng

    1   Fujian Province University, Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fuzhou, P. R. China (Ringgold ID: RIN12423)

  • Wangyang Li

    1   Fujian Province University, Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fuzhou, P. R. China (Ringgold ID: RIN12423)
    2   National Engineering Research Center of Chemical Fertilizer Catalyst, Fuzhou University, Fuzhou, P. R. China (Ringgold ID: RIN12423)

  • Qiuling Song 

    1   Fujian Province University, Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry at Fuzhou University, Fuzhou, P. R. China (Ringgold ID: RIN12423)
    3   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, P. R. China (Ringgold ID: RIN66519)
    4   State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, P. R. China (Ringgold ID: RIN12581)

Financial support from National Key Research & Development Program of China (2023YFF0723900), National Natural Science Foundation of China (21931013, 22271105 and 22401050), Natural Science Foundation of Fujian Province (2022J02009), China Postdoctoral Science Foundation (2025M780897) and Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang and China State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University are gratefully acknowledged.
Supported by: National Key Research & Development Program of China 2023YFF0723900 Supported by: Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang and China State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University Supported by: Natural Science Foundation of Fujian Province 2022J02009 Supported by: National Natural Science Foundation of China 21931013,22271105,22401050
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Graphical Abstract

Abstract

Six-membered ring scaffolds are widely recognized as prevalent structural motifs, which has consequently piqued the growing interest of the organic chemistry community. In this work, we report an Ni-catalyzed regio-, enantio-, and diastereoselective arylboration of 1,3-cyclohexadienes. This reaction utilizes readily accessible bis(pinacolato)diboron (B2pin2) and aryl iodides, offering a convenient approach to synthetically valuable chiral boronated 1,4-cis-cyclohexenes with excellent regio-, enantio-, and diastereoselectivity. Furthermore, the functionally diverse chiral boronated 1,4-cis-cyclohexene derivatives exhibit high reactivity in a variety of downstream transformations. Preliminary mechanistic studies, corroborated by Density Functional Theory (DFT) calculations, offer insights into the underlying causes of the observed regio- and enantioselectivity.

Keywords

Arylboration - Nickel catalysis - Cyclohexenes - Chiral organoborons - Asymmetric synthesis


Publication History

Received: 23 December 2025

Accepted after revision: 13 February 2026

Article published online:
26 February 2026

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