烯酮催化烷基烯转移的通用碳氢烷基化和烷基化

IF 16.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Xigeng Zhou, Yitu Wang, Xiaoke Shou, Yi Xu
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引用次数: 0

摘要

烯烃的烷基转移反应具有特殊的意义,但也具有一定的挑战性。在这里,我们报道了烯酮可以作为多种烷基烯源,用于各种亲核试剂的催化控制的选择性C-H烷基化和/或烷基化。以Y[N(TMS)2]3的催化量处理酮(或内酰胺)、烯酮和二芳基甲醇的混合物,得到相应的α-C-H键烷基化产物,由烯酮转移到酮/内酰胺,而烯酮与各种c -亲核试剂在KOH存在下的反应导致C-H烷基化。此外,还介绍了这些策略在某些生物活性分子的后期修饰或结构简化中的应用。这些烷基烯转移反应具有操作简单,反应条件温和,催化剂控制产物收率高的特点。这些结果不仅显示了易于获取和可回收的烯酮在碳氢烷基化和烷基化中作为多用途烷基烯源的巨大潜力,而且为缺乏电子的烯烃的氢脱烷基化提供了一种有吸引力和简洁的方法。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Versatile C–H alkylation and alkylidenation via catalytic alkylidene transfer of enones
The alkylidene transfer reactions of alkenes are of particular significance but challenging. Here, we report that enones can serve as diverse alkylidene sources for catalyst-controlled selective C–H alkylation and/or alkylidenation of various nucleophiles. Treatment of a mixture of ketone (or lactam), enone and diarylmethanol with a catalytic amount of Y[N(TMS)2]3, gave the corresponding α-C–H bond alkylation products derived from the alkylidene transfer from enones to ketones/lactams, whereas the reaction of enones with various C-nucleophiles in the presence of KOH as a catalyst resulted in C–H alkylidenation. Moreover, the application of these strategies for the late-stage modification or structural simplification of some bioactive molecules is also presented. These alkylidene transfer reactions are characterized by operational simplicity, mild reaction conditions, and remarkable catalyst-controlled product outcomes. These results not only demonstrate a significant potential for easily accessible and recyclable enones to serve as versatile alkylidene sources in C–H alkylation and alkylidenation, but also provide an attractive and concise method for hydrodealkylidenation of electron-deficient alkenes.
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来源期刊
CiteScore
26.60
自引率
6.60%
发文量
3549
审稿时长
1.5 months
期刊介绍: Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
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