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有机化学
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有机化学 ›› 2026, Vol. 46 ›› Issue (7): 2713-2722.DOI: 10.6023/cjoc202604052 上一篇    下一篇

研究论文

镍催化烯基三氟甲磺酸酯立体保持的烷基羰基化反应

陈海鸿a,†, 赵一譞a,†, 林杰a, 张潜b,*(), 李杰a,*()   

  1. a 苏州大学材料与化学化工学部 苏州市病原生物科学与抗感染医学重点实验室 江苏苏州 215123
    b 西交利物浦大学理学院 先进材料研究中心 江苏苏州 215123
  • 收稿日期:2026-04-30 修回日期:2026-06-04 发布日期:2026-06-26
  • 作者简介:

    †共同第一作者

  • 基金资助:
    国家自然科学基金(22322108); 国家自然科学基金(22571217); 江苏省自然科学基金(BK20231521); 苏州市科技计划(ZXL2024399)

Nickel-Catalyzed Stereoretentive Alkylcarbonylation of Alkenyl Triflates with Solid Alkylzinc Pivalates

Haihong Chena,†, Yixuan Zhaoa,†, Jie Lina, Qian Zhangb,*(), Jie Lia,*()   

  1. a MOE Key Laboratory of Geriatric Diseases and Immunology, Suzhou Key Laboratory of Pathogen Bioscience and Anti-infective Medicine, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
    b Department of Chemistry and Materials Science, Advanced Materials Research Center, School of Science, Xi'an-Jiaotong Liverpool University, Suzhou, Jiangsu 215123
  • Received:2026-04-30 Revised:2026-06-04 Published:2026-06-26
  • Contact: *E-mail: qian.zhang02@xjtlu.edu.cn;jjackli@suda.edu.cn
  • About author:

    †(The authors contributed equally to this work).

  • Supported by:
    National Natural Science Foundation of China(22322108); National Natural Science Foundation of China(22571217); Natural Science Foundation of Jiangsu Province(BK20231521); Science and Technology Program of Suzhou(ZXL2024399)

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α,β-不饱和酮是有机分子中非常重要的骨架结构, 能够通过各种转化构建复杂化合物. 目前, 通过过渡金属催化的直接羰基化交叉偶联策略高效构建α,β-不饱和酮的方法仍然存在底物范围有限的问题, 尤其是在构建烷基-烯基酮时烷基亲核试剂的普适性比较差. 此文报道了一种实用的镍催化四取代烯基三氟甲磺酸酯与一级和二级烷基锌试剂在101 kPa CO气体氛围下实现立体构型保持的羰基化反应. 该方法具有反应条件温和、操作简便、优异的立体选择性以及广泛的官能团兼容性等优点, 为制备α,β-不饱和酮提供了一种高效的途径.

关键词: 烷基羰基化, 镍催化, α,β-不饱和酮, 烷基特戊酸锌试剂

α,β-Unsaturated ketones are valuable prevalent skeletons in organic molecules, which can also be transformed to structurally diverse compounds. Thus far, the efficient construction of α,β-unsaturated ketones via transition-metal-catalyzed direct carbonylative cross-coupling strategies still suffer from limited substrate scope, particularly when constructing alkyl- alkenyl ketones. As such, we herein report a practical nickel-catalyzed stereoretentive carbonylation of tetrasubstituted alkenyl triflates with both primary and secondary alkylzinc pivalates under 101 kPa of CO gas. Moreover, this approach is distinguished by its mild conditions, simple operation, excellent stereoselectivity, and broad functional group compatibility, thereby providing an efficient method for the preparation of α,β-unsaturated ketones.

Key words: alkylcarbonylation, nickel catalyst, α,β-unsaturated ketones, alkylzinc pivalates