Mesoionic Carbene‐Catalyzed Formyl Alkylation of Aldehydes
Mesoionic Carbene‐Catalyzed Formyl Alkylation of Aldehydes
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介离子卡宾催化醛的甲酰烷基化
DOI：
10.1002/anie.202303478
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发表时间：
2023
期刊：
影响因子：
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通讯作者：
Yan, Xiaoyu
中科院分区：
文献类型：
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作者：
Liu, Chang;Zhang, Zengyu;Zhao, Liang‐Liang;Bertrand, Guy;Yan, Xiaoyu
酮是有机合成中最有用的官能团之一，并且它们通常在具有各种应用的广泛化合物中遇到。在本文中，我们描述了醛与非活化的仲烷基卤化物甚至伯烷基卤化物的介离子卡宾催化的偶联反应。这种无金属方法利用来自中离子卡宾（MIC）的去质子化Breslow中间体，其充当超电子供体并诱导烷基卤化物的单电子还原。这种温和的偶联反应具有广泛的底物范围并容许许多官能团，这允许通过后期官能化制备多种简单酮以及生物活性分子。
Ketones are among the most useful functional groups in organic synthesis, and they are commonly encountered in a broad range of compounds with various applications. Herein, we describe the mesoionic carbene‐catalyzed coupling reaction of aldehydes with non‐activated secondary and even primary alkyl halides. This metal‐free method utilizes deprotonated Breslow intermediates derived from mesoionic carbenes (MICs), which act as super electron donors and induce the single‐electron reduction of alkyl halides. This mild coupling reaction has a broad substrate scope and tolerates many functional groups, which allows to prepare a diversity of simple ketones as well as bio‐active molecules by late‐stage functionalization.