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<p>Benzyl boronic esters, as a class of organoboron compounds, are crucial intermediates in synthetic chemistry, yet the development of efficient approaches for the synthesis of these compounds remains a significant challenge. Herein, we described a nickel-catalyzed C(sp<sup>2</sup>)−C(sp<sup>3</sup>) Suzuki-type cross-coupling reaction of arylboronic acids with α-iodoboronates. The reaction offers an efficient method for synthesizing a variety of primary and secondary benzyl boronic esters. Moreover, the reaction proceeds under mild conditions and exhibits a broad substrate scope and high tolerance of functional groups. The practicality of this method has been demonstrated through gram-scale reactions and a variety of divergent transformations. Preliminary studies on enantioselective reactions have demonstrated promising stereoselectivity.</p>

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Nickel-catalyzed C(sp2)−C(sp3) cross-coupling to access benzyl Bpins of arylboronic acids with α-halo boronic esters

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月6日

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  • Yang Sun,
  • Chongwei Zhu,
  • Hui Wang

摘要

Benzyl boronic esters, as a class of organoboron compounds, are crucial intermediates in synthetic chemistry, yet the development of efficient approaches for the synthesis of these compounds remains a significant challenge. Herein, we described a nickel-catalyzed C(sp2)−C(sp3) Suzuki-type cross-coupling reaction of arylboronic acids with α-iodoboronates. The reaction offers an efficient method for synthesizing a variety of primary and secondary benzyl boronic esters. Moreover, the reaction proceeds under mild conditions and exhibits a broad substrate scope and high tolerance of functional groups. The practicality of this method has been demonstrated through gram-scale reactions and a variety of divergent transformations. Preliminary studies on enantioselective reactions have demonstrated promising stereoselectivity.