n -杂环碳催化脱羧交叉亲电偶联获得立体受阻酮

Xiangyu Zhuang , Hao Li , Tingting Wang , Hongyu Wang , Bo Tang
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引用次数: 0

摘要

虽然自由基NHC(氮杂环碳)催化已成为构建碳-碳(C-C)键以从羰基化合物(包括羧酸和醛)中生成增值酮的一种强有力的策略,但迄今为止,很大的进展通常集中在氧化还原中性NHC催化和氧化NHC催化上。交叉亲电偶联反应是避免使用预先形成的碳亲核有机金属试剂而形成C-C键的有力工具,但自由基NHC催化尚未得到很好的发展。在这里,我们证明了氮杂环碳(NHC)与锰(Mn)结合,可以促进芳香酸或衍生物与一系列广泛可用的亲电试剂的交叉偶联,以高收率提供各种立体体积大的酮。此外,其在生物活性化合物的简明合成中的应用也得到了进一步的强调。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

N-heterocyclic carbene-catalyzed decarboxylative cross-electrophile coupling to access sterically hindered ketones†

N-heterocyclic carbene-catalyzed decarboxylative cross-electrophile coupling to access sterically hindered ketones†
Although radical NHC (nitrogen-heterocyclic carbene) catalysis has emerged as a powerful strategy for constructing carbon–carbon (C–C) bonds to generate value-added ketones from carbonyl compounds including carboxylic acids and aldehydes, great advances were generally focused on redox-neutral NHC catalysis and oxidative NHC catalysis until now. Cross-electrophile coupling reactions as powerful tools for forming C–C bonds avoiding using preformed carbon nucleophilic organometallic reagents have not been well developed by radical NHC catalysis. Here, we demonstrate that nitrogen-heterocyclic carbene (NHC), in conjunction with manganese (Mn), can promote the cross-coupling of aromatic acids or derivatives with a wide array of broadly available electrophiles to deliver various sterically bulky ketones with high yields. In addition, its utility in the concise synthesis of biologically active compounds is further highlighted.
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CiteScore
7.80
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