Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 661-668.DOI: 10.6023/cjoc202010022 Previous Articles     Next Articles

Article

铁催化酮羰基的硼化反应合成α-羟基硼酸酯

朱庆a,b, 夏春谷a, 刘超a,*()   

  1. a 中国科学院兰州化学物理研究所 兰州 730000
    b 中国科学院大学 北京 100049
  • 收稿日期:2020-10-16 修回日期:2020-10-30 发布日期:2020-11-04
  • 通讯作者: 刘超
  • 作者简介:
    * Corresponding author. E-mail:
  • 基金资助:
    国家自然科学基金(21673261); 国家自然科学基金(91745110); 国家自然科学基金(21872156); 江苏省自然科学基金(BK20190002); 江苏省自然科学基金(BK20181194); 中国科学院青年创新促进会(2018458)

Iron-Catalyzed Borylation of Ketones to α-Hydroxyboronates

Qing Zhua,b, Chungu Xiaa, Chao Liua,*()   

  1. a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
    b University of Chinese Academy of Sciences, Beijing 100049
  • Received:2020-10-16 Revised:2020-10-30 Published:2020-11-04
  • Contact: Chao Liu
  • Supported by:
    the National Natural Science Foundation of China(21673261); the National Natural Science Foundation of China(91745110); the National Natural Science Foundation of China(21872156); the Natural Science Foundation of Jiangsu Province(BK20190002); the Natural Science Foundation of Jiangsu Province(BK20181194); and the Youth Innovation Promotion Association CAS(2018458)

Fe-catalyzed borylation of ketones to access tertiary α-hydroxyboronates has been demonstrated. In this transformation, commercially available FeBr2 was used as the catalyst, alcohols have been added to accelerate the transformation and avoid the side reaction. Various aliphatic ketones with different functional groups have been converted into tertiary α-hydroxyboronates. This transformation showed a particular tolerance for ketones with steric hinderance, which was distinguished from the traditional Cu catalyst. A gram scale reaction was also available. The alcoholic C—O functionalizations based onα-hydroxyboronates have been realized to access tertiary alkyl boronic esters, gem-diborylalkanes and gem- silylborylalkanes.

Key words: iron catalyst, α-hydroxyboronates, borylation, ketones