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2023 , Vol. 43 >Issue 6: 2197 - 2205

DOI: https://doi.org/10.6023/cjoc202209011

研究论文

无催化剂、无溶剂条件下炔烃和烯烃与儿茶酚硼烷的硼氢化反应

  • 卢凯 ,
  • 屈浩琦 ,
  • 陈樨 ,
  • 秋慧 ,
  • 郑晶 ,
  • 马猛涛
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  • 南京林业大学理学院 南京 210037

收稿日期: 2022-09-10

  修回日期: 2022-11-01

  网络出版日期: 2022-12-21

基金资助

国家自然科学基金(22171137); 国家自然科学基金(21772093); 江苏省研究生科研与实践创新计划(KYCX21_0874)

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Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane

  • Kai Lu ,
  • Haoqi Qu ,
  • Xi Chen ,
  • Hui Qiu ,
  • Jing Zheng ,
  • Mengtao Ma
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  • College of Science, Nanjing Forestry University, Nanjing 210037
* E-mail: ;

Received date: 2022-09-10

  Revised date: 2022-11-01

  Online published: 2022-12-21

Supported by

National Natural Science Foundation of China(22171137); National Natural Science Foundation of China(21772093); Postgraduate Research & Practice Innovation Program of Jiangsu Province(KYCX21_0874)

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摘要

报道了无催化剂和无溶剂条件下炔烃和烯烃与儿茶酚硼烷的硼氢化反应, 各种芳香族和脂肪族炔烃和烯烃底物分别以高产率和高区域/立体选择性成功地转化为相应的反马氏烯基和烷基硼酸酯产物. 克级硼氢化和多用途转化反应显示了其在实际应用中的巨大潜力. 在相应密度泛函理论(DFT)计算的基础上, 提出了一种可能的反应机理.

关键词： 绿色化学; 硼氢化; 无催化剂; 炔烃; 烯烃

本文引用格式

卢凯 , 屈浩琦 , 陈樨 , 秋慧 , 郑晶 , 马猛涛 . 无催化剂、无溶剂条件下炔烃和烯烃与儿茶酚硼烷的硼氢化反应[J]. 有机化学, 2023 , 43(6) : 2197 -2205 . DOI: 10.6023/cjoc202209011

Abstract

A catalyst-free and solvent hydroboration of alkynes and alkenes with catecholborane was reported. Various alkynes and alkenes including aromatic and aliphatic groups were smoothly converted into the corresponding anti-Markovnikov alkenyl and alkyl boronate esters in high yields and high regio/stereoselectivity at room temperature and 50 ℃, respectively. The gram-scale hydroboration and further versatile conversions demonstrated great potential in the practical application. A plausible reaction mechanism was proposed based on the corresponding density function theory (DFT) calculations.

Key words： green chemistry; hydroboration; catalyst-free; alkyne; alkene

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