受激宝石二氟烯烃光催化菲萘分子间脱芳环加成反应

IF 11.5 Q1 CHEMISTRY, PHYSICAL

Chem Catalysis Pub Date : 2024-12-17 DOI:10.1016/j.checat.2024.101200

Yunxiao Zhang, Youyuan Guo, Yizhi Zhang, Shanshan Liu, Xiao Shen

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引用次数: 0

摘要

脱芳环加成是一种由简单前驱体构建三维（3D）复杂分子的重要方法，但难以激发许多芳烃限制了该方法的应用。在此，我们报道了菲和萘与激发的宝石二氟烯烃进行光催化分子间[2 + 2]/[4 + 2]环加成反应，合成了宝石二氟环丁烷和宝石二氟环己烷。先前涉及受激菲和萘的脱芳环加成反应需要缺电子取代基来降低其激发态能量，从而允许发生能量转移催化。我们的策略涉及激发态宝石-二氟烯烃与基态菲和萘进行脱芳环加成反应，使其不仅可以耐受缺电子芳烃，还可以耐受电子中性芳烃和富电子芳烃。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photocatalytic intermolecular dearomative cycloaddition of phenanthrenes and naphthalenes with excited gem-difluoroalkenes

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Photocatalytic intermolecular dearomative cycloaddition of phenanthrenes and naphthalenes with excited gem-difluoroalkenes

Dearomative cycloaddition is a crucial method for constructing three-dimensional (3D) complex molecules from simple precursors, but the difficulty in exciting many arenes limits the application of this method. Herein, we report a photocatalytic intermolecular dearomative [2 + 2]/[4 + 2] cycloaddition of phenanthrenes and naphthalenes with excited gem-difluoroalkenes for the synthesis of fused gem-difluorocyclobutanes and gem-difluorocyclohexanes. Previous dearomative cycloaddition reactions involving excited phenanthrenes and naphthalenes required electron-deficient substituents to lower their excited-state energies, allowing for energy-transfer catalysis to occur. Our strategy involves excited-state gem-difluoroalkenes undergoing dearomative cycloaddition reactions with ground-state phenanthrenes and naphthalenes, enabling it to tolerate not only electron-deficient arenes but also electron-neutral and electron-rich arenes.

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来源期刊

Chem Catalysis

CiteScore

10.50

自引率

6.40%

发文量

期刊介绍： Chem Catalysis is a monthly journal that publishes innovative research on fundamental and applied catalysis, providing a platform for researchers across chemistry, chemical engineering, and related fields. It serves as a premier resource for scientists and engineers in academia and industry, covering heterogeneous, homogeneous, and biocatalysis. Emphasizing transformative methods and technologies, the journal aims to advance understanding, introduce novel catalysts, and connect fundamental insights to real-world applications for societal benefit.