摘要
报道了一种铁催化烷基酮类化合物硼化合成三级α-羟基硼酸酯的反应,使用了可商业购买的FeBr_(2)作为催化剂,加入醇作为添加剂来加速反应的进行,同时避免副反应的发生.通过该方法合成了一系列三级α-羟基硼酸酯化合物,反应具有很好的底物兼容性以及官能团兼容性.该铁催化剂对于大位阻的酮类化合物的硼化反应,表现出优于铜催化的活性.同时该反应可应用于克级规模的制备,随后通过对三级α-羟基硼酸酯的C-O键进行官能化,将所得的三级α-羟基硼酸酯转化为三级烷基硼酸酯以及偕二硼、偕硅硼类化合物.
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 on α-hydroxyboronates have been realized to access tertiary alkyl boronic esters, gem-diborylalkanes and gemsilylborylalkanes.
作者
朱庆
夏春谷
刘超
Zhu Qing;Xia Chungu;Liu Chao(State Key Laboratory for Oxo Synthesis and Selective Oxidation,Lanzhou Institute of Chemical Physics,Chinese Academy of Sciences,Lanzhou 730000;University of Chinese Academy of Sciences,Beijing 100049)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2021年第2期661-668,共8页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(Nos.21673261,91745110,21872156)
江苏省自然科学基金(Nos.BK20190002,BK20181194)
中国科学院青年创新促进会(No.2018458)资助项目.
