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可见光诱导的脱羧环化反应。

Visible-light-induced decarboxylative cyclization.

作者信息

Das Suven

机构信息

Department of Chemistry, Rishi Bankim Chandra College for Women, Naihati, 24-Parganas (N), Pin-743165, India.

出版信息

Org Biomol Chem. 2025 Jan 29;23(5):1016-1066. doi: 10.1039/d4ob01744g.

DOI:10.1039/d4ob01744g
PMID:39688151
Abstract

The application of visible light as an energy source provides a new avenue in organic transformation due to its mildness, efficiency and selectivity. In fact, recent years have witnessed remarkable advances in photoinduced decarboxylative coupling reactions involving carboxylic acids and their derivatives. Under appropriate photoredox conditions they undergo single electron transfer (SET), resulting in reactive radicals which can assemble with suitable reaction partners. Many types of carboxylic acid derivatives, such as amino acids, -hydroxy phthalimide (NHPI) esters, α-keto acids, aliphatic/aromatic carboxylic acids, and [bis(difluoroacetoxy)iodo]benzene, can couple with a wide variety of substrates to build structurally complex molecules. The present review summarizes the last five years of progress (2020-2024) in the decarboxylative cyclization of carboxylic acids for constructing carbo-/heterocycles under visible-light irradiation. Annulation could be attained organophotocatalysis (4CzIPN, g-CN, Eosin Y, methylene blue, .), metallaphotocatalysis or photocatalyst-free approaches. With an emphasis on the mechanistic rationales and scope of the reactions, this review focuses on recent trends in this emerging area.

摘要

可见光作为一种能源的应用,因其温和性、高效性和选择性,为有机转化提供了一条新途径。事实上,近年来光诱导脱羧偶联反应在涉及羧酸及其衍生物方面取得了显著进展。在适当的光氧化还原条件下,它们会发生单电子转移(SET),产生能够与合适反应伙伴结合的活性自由基。许多类型的羧酸衍生物,如氨基酸、N-羟基邻苯二甲酰亚胺(NHPI)酯、α-酮酸、脂肪族/芳香族羧酸以及[双(二氟乙酰氧基)碘]苯,都可以与各种各样的底物偶联,构建结构复杂的分子。本综述总结了过去五年(2020 - 2024年)在可见光照射下羧酸脱羧环化构建碳环/杂环方面的进展。环化可以通过有机光催化(4CzIPN、g-C3N4、曙红Y、亚甲基蓝等)、金属光催化或无光催化剂方法实现。本综述着重于反应的机理原理和范围,聚焦于这一新兴领域的最新趋势。

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