双（五氟苯基）硼烯醇酯醛缩反应合成α-五氟苯基取代α，β-不饱和羰基化合物。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-11 DOI:10.1021/acs.orglett.5c03342

Souta Yuruka, , , Masatoshi Shibuya*, , and , Yoshihiko Yamamoto*,

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引用次数: 0

摘要

α-五氟苯基取代α，β-不饱和羰基化合物是合成全氟芳烃的重要原料。醛醇与五氟苯基取代烯醇酯缩合是一种高效的合成方法。本研究表明，具有五氟苯基的双（五氟苯基）硼烯醇化物易于与醛类进行醛醇加成。硼酸的后续消去得到α-五氟苯基取代的α，β-不饱和羰基化合物。实验结果强调了硼中心强刘易斯酸在醛醇加成和硼酸消除过程中的重要作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Aldol Condensation of Bis(pentafluorophenyl)boron Enolates for the Synthesis of α-Pentafluorophenyl-Substituted α,β-Unsaturated Carbonyl Compounds

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Aldol Condensation of Bis(pentafluorophenyl)boron Enolates for the Synthesis of α-Pentafluorophenyl-Substituted α,β-Unsaturated Carbonyl Compounds

α-Pentafluorophenyl-substituted α,β-unsaturated carbonyl compounds are valuable for synthesizing perfluoroarenes. Aldol condensation with pentafluorophenyl-substituted enolates is a highly effective method for their synthesis. This study demonstrates that bis(pentafluorophenyl)boron enolates, featuring a pentafluorophenyl group, readily undergo aldol additions with aldehydes. Subsequent elimination of borinic acid yields α-pentafluorophenyl-substituted α,β-unsaturated carbonyl compounds. Experimental results highlight the crucial role of strong Lewis acidity at the boron center in both aldol addition and borinic acid elimination.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.