Access to -Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide

Guo Chun-Xiao; Zhang Wen-Zhen; Zhou Hui; Zhang Ning; Lu Xiao-Bing

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Access to -Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide

机译：通过二氧化碳的芳香亚胺的Uppolung羧基化获得-Arylglycines

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A straightforward and transition-metal-free approach for the efficient synthesis of -arylglycine derivatives from aromatic imines and carbon dioxide was enabled by an umpolung carboxylation reaction. Various substituted diphenylmethimines underwent the carboxylation smoothly with carbon dioxide in the presence of potassium tert-butoxide and 18-crown-6 to give the corresponding carboxylated products in good to high yields. Besides the enhancement of the solubility of potassium tert-butoxide in THF, 18-crown-6 also plays key roles in suppressing the reverse protonation or 1, 3-proton shift isomerization as well as by stabilizing the carboxylated intermediate.

机译：通过杂酚羧化反应实现了从芳族亚胺和二氧化碳有效合成-芳基甘氨酸衍生物的直接且无过渡金属的方法。在叔丁醇钾和18-crown-6的存在下，各种取代的二苯甲亚胺与二氧化碳顺利地进行了羧化反应，以高至高收率得到了相应的羧化产物。除了提高叔丁醇钾在THF中的溶解度外，18-crown-6在抑制反向质子化或1，3质子转移异构化以及稳定羧化中间体方面也起着关键作用。

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《Chemistry: A European journal》 |2016年第48期|共4页
作者
Guo Chun-Xiao; Zhang Wen-Zhen; Zhou Hui; Zhang Ning; Lu Xiao-Bing;
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正文语种 eng
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关键词
amino acids; carbon dioxide fixation; carboxylation; transition-metal-free synthesis; umpolung;

机译：氨基酸;二氧化碳固定;羧化;无过渡金属合成;活性;

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1. Access to -Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide [J] . Guo Chun-Xiao, Zhang Wen-Zhen, Zhou Hui, Chemistry: A European journal . 2016,第48期

机译：通过二氧化碳的芳香亚胺的Uppolung羧基化获得-Arylglycines
2. Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide [J] . Mita T., Sugawara M., Hasegawa H., The Journal of Organic Chemistry . 2012,第5期

机译：α-酰胺基和α-乙酰氧基锡烷与二氧化碳的羧化反应合成芳基甘氨酸和扁桃酸衍生物
3. A synthesis of α-amino acids via direct reductive carboxylation of imines with carbon dioxide [J] . Ajay A. Sathe, Douglas R. Hartline, Alexander T. Radosevich Chemical Communications . 2013,第44期

机译：亚胺与二氧化碳的直接还原羧化合成α-氨基酸
4. Sequestration of carbon dioxide by enzymatically-catalyzed carboxylation of aromatics [C] . Harrison B. Rose, Andreas S. Bommarius AIChE Annual Meeting . 2014

机译：通过酶促催化的芳烃羧化催化二氧化碳的固化
5. I. Coating of electrically conducting polymeric films on the surface of non-conducting substrate. II. Carboxylation of aromatic alcohols under carbon dioxide pressure. III. Low temperature phase-transfer catalyzed autoxidation of p-xylene for the production of terephthalic acid. [D] . Deng, Fenghua. 1996

机译：I.在不导电基底的表面上涂覆导电聚合物膜。二。在二氧化碳压力下芳族醇的羧化。三，对二甲苯的低温相转移催化自氧化，用于生产对苯二甲酸。
6. Mechanistic study of the rhodium-catalyzed carboxylation of simple aromatic compounds with carbon dioxide [O] . Takuya Suga, Takanobu Saitou, Jun Takaya, 2017

机译：铑简单催化芳香化合物与二氧化碳羧化反应的机理研究
7. Mechanistic study of the rhodium-catalyzed carboxylation of simple aromatic compounds with carbon dioxide [O] . Takuya Suga, Takanobu Saitou, Jun Takaya, 2017

机译：用二氧化碳的简单芳族化合物铑催化羧化的机械研究

Access to -Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide

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