有机化学 ›› 2022, Vol. 42 ›› Issue (9): 2888-2897.DOI: 10.6023/cjoc202201045 上一篇    下一篇

研究论文

蓝光诱导的1,3-二酮C(CO)—C键卡宾插入反应

巴聃a,b, 程国林a,*()   

  1. a 华侨大学材料科学与工程学院 分析测试中心 厦门市光电材料及其先进制造重点实验室 福建厦门 361021
    b 三峡大学材料与化工学院 湖北宜昌 443002
  • 收稿日期:2022-01-26 修回日期:2022-05-28 发布日期:2022-06-08
  • 通讯作者: 程国林
  • 基金资助:
    国家自然科学基金(22071068)

Blue Light Induced Insertion of Carbene into C(CO)—C Bonds of 1,3-Diones

Dan Baa,b, Guolin Chenga()   

  1. a Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, the Instrumental Analysis Center, College of Materials Science and Engineering, Huaqiao University, Xiamen, Fujian 361021
    b School of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
  • Received:2022-01-26 Revised:2022-05-28 Published:2022-06-08
  • Contact: Guolin Cheng
  • Supported by:
    National Natural Science Foundation of China(22071068)

可见光诱导被认为是绿色化学合成中的理想“工具”. 可见光诱导的反应具有条件温和、设备简单及副产物少等优点, 逐渐发展成为有机合成领域重要的方法之一. 报道了蓝光诱导溴化锂促进的重氮酸酯卡宾插入1,3-二酮底物C(CO)—C键的反应, 合成了一系列含全碳季碳中心的1,4-二酮化合物. 该合成方法具有良好的底物普适性和官能团兼容性, 是一种理想高效的1,4-二酮化合物合成策略.

关键词: 蓝光, 路易斯酸, 卡宾, 1, 3-二酮, 碳碳键断裂

Visible light is an ideal “tool” for the green chemical synthesis. Visible light-induced reactions show such advantages as mild reaction conditions, simple equipments and less by-products. Therefore, it has gradually become an important method in organic synthesis. Herein an blue light induced LiBr-promoted carbene insertion reaction of diazoesters into C(CO)—C bonds of 1,3-diones for the synthesis of a wide range of all-carbon quaternary center-containing 1,4-dione derivatives is reported. The method features good substrate universality and functional group compatibility, and therefore is an ideal and efficient strategy for the synthesis of 1,4-diones.

Key words: blue light, Lewis acid, carbene, 1, 3-dione, carbon-carbon bond cleavage