Anomeric Amide-Enabled Alkene-Arene and Alkene-Alkene Aminative Coupling.

IF 16.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Colin Stein, Jasper L Tyler, Julius Wiener, Florian Boser, Constantin G Daniliuc, Frank Glorius
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引用次数: 0

Abstract

Despite the prominence of C-N bond forming cross-coupling reactions as a strategy to assemble molecular fragments, aminative coupling approaches, in which two fragments are assembled directly at the heteroatom, represents a rarely exploited retrosynthetic strategy. Herein, we report the design, synthesis, and implementation of an anomeric amide reagent capable of promoting highly regioselective aminative alkene-arene and alkene-alkene coupling reactions. This transformation follows a sequence of catalyst-free chloroamination, N-deprotection, and formal nitrene functionalization, all in one-pot. Due to the simplicity of both the protocol and the building blocks required, high-throughput experimentation (HTE) was employed to rapidly and efficiently explore a wide range of chemical space and determine the limits of reactivity. In addition, alternative reactivity modes from the functionalized intermediates delivered by this protocol demonstrate the divergent nature of this aminative coupling strategy.

烯-烯和烯-烯氨化偶联。
尽管 C-N 键形成的交叉偶联反应作为一种组装分子片段的策略非常突出,但氨基偶联方法(其中两个片段直接在杂原子上组装)是一种很少被利用的逆合成策略。在此,我们报告了能够促进高区域选择性氨基烯-炔和烯-烃偶联反应的异构体酰胺试剂的设计、合成和实施。这种转化遵循无催化剂氯代、N-脱保护和正式腈官能化的顺序,全部在一锅内完成。由于方案和所需构件都很简单,因此采用了高通量实验(HTE)来快速有效地探索广泛的化学空间,并确定反应性的极限。此外,该方案提供的官能化中间体的替代反应模式也证明了这种氨基偶联策略的多样性。
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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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