Citation: 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 shu

n-Bu₄NBr Catalyzed Brook Rearrangement/Alkylation Reaction

School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000

Corresponding author: Han Man-Yi, hanmy10@126.com
Received Date: 31 May 2020
Revised Date: 11 July 2020
Available Online: 5 August 2020
Fund Project: 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 Provincethe Natural Science Foundation of Anhui Province 1708085QB39the National Natural Science Foundation of China 21602073

Figures(4)

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.
- phase transfer catalysis,
- bimolecular nucleophilic substitution (S_N2) reaction,
- alkylation,
- Brook rearrangement
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n-Bu₄NBr Catalyzed Brook Rearrangement/Alkylation Reaction