Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4274-4283.DOI: 10.6023/cjoc202005093 Previous Articles     Next Articles


韩满意, 潘虹, 姚紫云, 李琦   

  1. 淮北师范大学化学与材料科学学院 安徽淮北 235000
  • 收稿日期:2020-05-31 修回日期:2020-07-11 发布日期:2020-08-06
  • 通讯作者: 韩满意
  • 基金资助:

n-Bu4NBr Catalyzed Brook Rearrangement/Alkylation Reaction

Han Man-Yi, Pan Hong, Yao Ziyun, Li Qi   

  1. School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000
  • Received:2020-05-31 Revised:2020-07-11 Published:2020-08-06
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21602073), the Natural Science Foundation of Anhui Province (No. 1708085QB39) and the Young Scholars in Wanjiang Scholars Program of Anhui Province.

A novel Brook rearrangement/alkylation reaction sequence of tertiary α-silyl alcohols has been developed using n-Bu4NBr as the phase transfer catalyst (PTC). A number of tertiary α-silyl alcohols are applicable to the reaction, affording the products with a quaternary carbon center in high yields (up to 71%). Moreover, the carbanions generated after the Brook rearrangement could be stabilized by the electron-withdrawing group, depressing the Brook rearrangement/protonation reaction.

Key words: phase transfer catalysis, bimolecular nucleophilic substitution (SN2) reaction, alkylation, Brook rearrangement