Metal-free photoinduced-radical hydrocyclization of 2-isocyanides: a unified synthetic approach to facilely assemble diverse N-heteroarenes†

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-10-02 DOI:10.1039/D4GC03774J

Ziyi Wang, Haonan Wei, Jinrong Du and Zhijun Zuo

引用次数: 0

Abstract

α-Unsubstituted aromatic N-heterocycles are a family of broadly used building blocks that play an integral role in drugs, agrochemicals, and materials. However, accessing diverse α-unsubstituted N-heteroarenes in a single strategy is challenging but highly desirable. Thus, a novel and unified photoinduced-radical hydrocyclization of 2-isocyanides is described for rapid assembling of various N-heteroarenes. The reaction features mild and sustainable reaction conditions with broad substrate scope and excellent functional group compatibilities. The potential synthetic utilization is highlighted by the facile synthesis of some biologically active natural alkaloids. Moreover, the mechanism studies indicated that the single-electron reduction/protonation is the key process of the transformation.

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2-异氰酸酯的无金属光诱导-自由基加氢环化：轻松组装多种 N-杂环†的统一合成方法

α-未取代芳香族 N-杂环是一个广泛使用的构筑基团家族，在药物、农用化学品和材料中发挥着不可或缺的作用。然而，通过单一策略获得多种α-未取代的 N-杂环具有挑战性，但也是非常理想的。因此，本文介绍了一种新颖、统一的 2-异氰酸酯光诱导-自由基加氢环化反应，用于快速组装各种 N-己烯。该反应的特点是反应条件温和且可持续，底物范围广，官能团兼容性好。通过轻松合成一些具有生物活性的天然生物碱，凸显了其潜在的合成用途。此外，机理研究表明，单电子还原/质子化是转化的关键过程。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.