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

IF 4.7 3区 材料科学 Q1 ENGINEERING, ELECTRICAL & ELECTRONIC ACS Applied Electronic Materials Pub Date : 2024-03-28 DOI:10.1093/bulcsj/uoae038
Ban Kinoshita, Saki Maejima, Yuta Niki, K. Mitsudo, Seiji Suga, Hideki Yorimitsu
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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。
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来源期刊
CiteScore
7.20
自引率
4.30%
发文量
567
期刊介绍: ACS Applied Electronic Materials is an interdisciplinary journal publishing original research covering all aspects of electronic materials. The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrate knowledge in the areas of materials science, engineering, optics, physics, and chemistry into important applications of electronic materials. Sample research topics that span the journal's scope are inorganic, organic, ionic and polymeric materials with properties that include conducting, semiconducting, superconducting, insulating, dielectric, magnetic, optoelectronic, piezoelectric, ferroelectric and thermoelectric. Indexed/​Abstracted: Web of Science SCIE Scopus CAS INSPEC Portico
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