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Visible-Light-Induced Decarboxylative Acylation of Pyridine N-Oxides with α-Oxocarboxylic Acids Using Fluorescein Dimethylammonium as a Photocatalyst
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-03-26 , DOI: 10.1002/adsc.202100168
wenyi chu 1 , Chuanfu Hou 2 , Souneng Sun 2 , Ziqi Liu 2 , Hui Zhang 2 , Yue Liu 3 , Qi An 2 , Jian Zhao 2 , Junjie Ma 1 , Zhizhong Sun 3
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-03-26 , DOI: 10.1002/adsc.202100168
wenyi chu 1 , Chuanfu Hou 2 , Souneng Sun 2 , Ziqi Liu 2 , Hui Zhang 2 , Yue Liu 3 , Qi An 2 , Jian Zhao 2 , Junjie Ma 1 , Zhizhong Sun 3
Affiliation
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Herein, the development of a visible-light-induced catalytic system to achieve the decarboxylative acylation of pyridine N-oxides with α-oxocarboxylic acids, at room temperature and using the organic dye fluorescein dimethylammonium as a new type of photocatalyst, is reported. A series of 2-arylacylpyridine N-oxides were selectively synthesized in moderate to good yields by controlling the polarity of the reaction solvent. The developed strategy was successfully applied in the synthesis of an important intermediate of the drug, acrivastine, on a gram scale. Notably, this is the first time that fluorescein dimethylammonium has been used to catalyze the Minisci-type C−H decarboxylative acylation reaction. The mechanism of decarboxylative acylation was studied by capturing adducts of acyl radicals and 1,1-diphenylethylene to confirm a radical mechanism. The disclosed catalytic system provides a green synthetic strategy for decarboxylative acylation without the use of additional oxidants or metal catalysts.
中文翻译：
使用荧光素二甲基铵作为光催化剂，可见光诱导吡啶 N-氧化物与 α-氧代羧酸脱羧酰化
在此，报道了在室温下使用有机染料荧光素二甲基铵作为新型光催化剂实现吡啶N-氧化物与 α-氧代羧酸脱羧酰化的可见光诱导催化体系的开发。一系列2-芳酰基吡啶N通过控制反应溶剂的极性，以中等至良好的产率选择性合成 - 氧化物。所开发的策略已成功应用于克级规模的药物重要中间体阿伐斯汀的合成。值得注意的是，这是荧光素二甲基铵首次用于催化 Minisci 型 C−H 脱羧酰化反应。通过捕获酰基自由基和 1,1-二苯基乙烯的加合物来研究脱羧酰化的机制，以确认自由基机制。所公开的催化体系为脱羧酰化提供了一种绿色合成策略，无需使用额外的氧化剂或金属催化剂。
更新日期：2021-03-26
中文翻译：
使用荧光素二甲基铵作为光催化剂，可见光诱导吡啶 N-氧化物与 α-氧代羧酸脱羧酰化
在此，报道了在室温下使用有机染料荧光素二甲基铵作为新型光催化剂实现吡啶N-氧化物与 α-氧代羧酸脱羧酰化的可见光诱导催化体系的开发。一系列2-芳酰基吡啶N通过控制反应溶剂的极性，以中等至良好的产率选择性合成 - 氧化物。所开发的策略已成功应用于克级规模的药物重要中间体阿伐斯汀的合成。值得注意的是，这是荧光素二甲基铵首次用于催化 Minisci 型 C−H 脱羧酰化反应。通过捕获酰基自由基和 1,1-二苯基乙烯的加合物来研究脱羧酰化的机制，以确认自由基机制。所公开的催化体系为脱羧酰化提供了一种绿色合成策略，无需使用额外的氧化剂或金属催化剂。
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