无催化剂及无溶剂光引发下氮杂芳烃的自由基脱羧酰基化反应

doi:10.6023/cjoc202509006

研究论文

无催化剂及无溶剂光引发下氮杂芳烃的自由基脱羧酰基化反应

黄涎廷^a, 沈小倩^a, 王庆许^a, 柳哲怀^b, 黄也^b, 柳忠全^*,a

^a南京中医药大学江苏南京 210023;
^a句容碧桂园学校江苏镇江 212446

收稿日期:2025-09-05 修回日期:2025-11-18
基金资助:
国家自然科学基金(No. 22371129)资助项目.

A Catalyst and Solvent-Free Photochemical Acylation of N-Heteroarenes with Keto Acids

Xianting Huang^a, Xiaoqian Shen^a, Qingxu Wang^a, Zhehuai Liu^b, Ye Huang^b, Zhong-Quan Liu^*,a

^aNanjing University of Chinese Medicine, Nanjing 210023;
^bJurong Country Garden School, Zhenjiang 212446

Received:2025-09-05 Revised:2025-11-18
Contact: *E-mail: liuzhq@lzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 22371129).

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摘要/Abstract

氮杂芳基酮化合物是一类重要的合成中间体,其骨架结构广泛存在于天然产物、药物分子和材料中。通过酮酸脱羧自由基酰基化氮杂环是一种有效地构建氮杂芳基酮化合物的策略。然而,已报道的合成方法一般都需要过渡金属催化剂、大量的化学氧化剂、光敏剂等,限制了它们的工业应用。在此,我们报道一种绿色且实用的策略来合成此类化合物。对氮杂芳烃与α-酮酸的混合物进行蓝光照射,可以高产率、高选择性且可大规模地合成相应的酰基化N-杂芳烃。该体系不需要任何光敏剂、催化剂、氧化剂或溶剂。此外,值得注意的是,该体系甚至不需要持续的蓝光照射,只需要光引发就足以促进这一过程。

关键词: 自由基化学, 光化学, 脱羧, 酰基化, 氮杂芳烃, 无溶剂

The N-heteroaryl ketones are an important class of synthetic intermediates, and their skeletal structures are widely found in natural products, drug molecules, and materials. Acylation of N-heterocycles by keto acid decarboxylation is an effective strategy for constructing N-heteroaryl ketone compounds. However, the reported synthesis methods generally require transition-metal catalysts, a large amount of chemical oxidants, photosensitizers, etc., which limits their industrial applications. Herein, we report a green and practical strategy for synthesizing such compounds. Blue light irradiation of the mixture of N-heteroaromatics and α-ketoacids can lead to high-yield, high selectivity, and large-scale synthesis of the corresponding acylated N-heteroarenes. This system does not require any photosensitizers, catalysts, oxidants, or solvents. In addition, it is worth noting that this system does not even require continuous blue light irradiation, only light triggering is sufficient to promote this process.

Key words: Free-radical chemistry, Photochemistry, Decarboxylation, Acylation, N-Heteroarenes, Solvent-free

引用此文

黄涎廷, 沈小倩, 王庆许, 柳哲怀, 黄也, 柳忠全. 无催化剂及无溶剂光引发下氮杂芳烃的自由基脱羧酰基化反应[J]. 有机化学, doi: 10.6023/cjoc202509006.

Xianting Huang, Xiaoqian Shen, Qingxu Wang, Zhehuai Liu, Ye Huang, Zhong-Quan Liu. A Catalyst and Solvent-Free Photochemical Acylation of N-Heteroarenes with Keto Acids[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202509006.

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