n-Bu4NBr Catalyzed Brook Rearrangement/Alkylation Reaction

doi:10.6023/cjoc202005093

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

四丁基溴化铵催化的布鲁克重排/烷基化反应

韩满意, 潘虹, 姚紫云, 李琦

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 E-mail:hanmy10@126.com
基金资助:
国家自然科学基金（No.21602073）、安徽省自然科学基金（No.1708085QB39）和安徽省青年皖江学者资助项目.

n-Bu₄NBr Catalyzed Brook Rearrangement/Alkylation Reaction

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

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.

1. cjoc202005093.pdf(5983KB)

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.

Key words: phase transfer catalysis, bimolecular nucleophilic substitution (S_N2) reaction, alkylation, Brook rearrangement

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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.

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四丁基溴化铵催化的布鲁克重排/烷基化反应

n-Bu₄NBr Catalyzed Brook Rearrangement/Alkylation Reaction

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