n-Bu4NBr Catalyzed Brook Rearrangement/Alkylation Reaction

  • Han Man-Yi ,
  • Pan Hong ,
  • Yao Ziyun ,
  • Li Qi
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  • School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000

Received date: 2020-05-31

  Revised date: 2020-07-11

  Online 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.

Abstract

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.

Cite this article

Han Man-Yi , Pan Hong , Yao Ziyun , Li Qi . n-Bu4NBr Catalyzed Brook Rearrangement/Alkylation Reaction[J]. Chinese Journal of Organic Chemistry, 2020 , 40(12) : 4274 -4283 . DOI: 10.6023/cjoc202005093

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