[1,2]-Retro-Brook Rearrangement Induced by Electrochemical Reduction of Silyl Enolates

IF 3.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Bulletin of the Chemical Society of Japan Pub Date : 2024-03-28 DOI:10.1093/bulcsj/uoae038

Ban Kinoshita, Saki Maejima, Yuta Niki, K. Mitsudo, Seiji Suga, Hideki Yorimitsu

引用次数: 0

Abstract

Electrochemical reduction of the trimethylsilyl enolates of alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence of 1) single-electron reduction of the silyl enolate, 2) protonation with a phenol, 3) another single-electron reduction to form siloxy-substituted benzylic anion, and 4) the pivotal retro-Brook rearrangement.

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硅烯醇酯电化学还原引发的 [1,2]-Retro-Brook 重排反应

电化学还原烷基芳基酮的三甲基硅烯醇化物可诱导逆布鲁克重排反应，生成 1-芳基-1-三甲基硅烷-1-醇。转化过程依次为：1）硅烷基烯醇的单电子还原；2）与苯酚的质子化；3）另一次单电子还原以形成硅氧基取代的苄基阴离子；4）关键的逆布鲁克重排。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Bulletin of the Chemical Society of Japan 化学-化学综合

CiteScore

6.40

自引率

5.00%

发文量

194

审稿时长

3-8 weeks

期刊介绍： The Bulletin of the Chemical Society of Japan (BCSJ) is devoted to the publication of scientific research papers in the fields of Theoretical and Physical Chemistry, Analytical and Inorganic Chemistry, Organic and Biological Chemistry, and Applied and Materials Chemistry. BCSJ appears as a monthly journal online and in advance with three kinds of papers (Accounts, Articles, and Short Articles) describing original research. The purpose of BCSJ is to select and publish the most important papers with the broadest significance to the chemistry community in general. The Chemical Society of Japan hopes all visitors will notice the usefulness of our journal and the abundance of topics, and welcomes more submissions from scientists all over the world.