Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids

Wang Hongxiang; Shao Ying; Zheng Hao; Wang Hanghang; Cheng Jiang; Wan Xiaobing

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Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids

机译：氰乙酸作为掩盖的亲电试剂：胺和羧酸的无过渡金属的氰甲基化

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Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of alpha-aminonitriles and cyanomethyl esters with good yields and excellent func- tionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. lodoacetonitrile was generated in situ from the iodination decarboxylation of cyanoacetic acid in this transformation.

机译：使用氰基乙酸作为掩蔽的亲电试剂，开发了一种新的胺和羧酸的氰基甲基化反应，以高收率和出色的功能耐受性生产了多种α-氨基腈和氰基甲基酯。该方案具有操作简单，试剂便宜和底物范围广的特点。在该转化过程中，氰基乙酸的碘化脱羧反应原位生成了碘乙腈。

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《Chemistry: A European journal》 |2015年第50期|共5页
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Wang Hongxiang; Shao Ying; Zheng Hao; Wang Hanghang; Cheng Jiang; Wan Xiaobing;
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1. Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids [J] . Wang Hongxiang, Shao Ying, Zheng Hao, Chemistry: A European journal . 2015,第50期

机译：氰乙酸作为掩盖的亲电试剂：胺和羧酸的无过渡金属的氰甲基化
2. Nucleophile‐electrophile interactions in the reaction of oxiranes with carboxylic acids in the presence of tertiary amines [J] . Bakhtin Stanislav, Shved Elena, Bespalko Yuliia Journal of Physical Organic Chemistry . 2017,第12期

机译：在叔胺存在下，羧酸与羧酸反应的亲核试剂亲电相互作用
3. Synthesis of 2-Amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carboxylic Acids Derivatives by Recyclization of 5-Arylfuran-2,3-diones under the Action of Cyanoacetic Acid Derivatives [J] . Ivanov D. V., Igidov N. M., Rubtsov A. E. Russian Journal of Organic Chemistry . 2016,第5期

机译：5-芳基呋喃-2,3-二酮在该作用下的环化反应合成2-氨基-5-（2-芳基-2-氧代亚乙基）-4-氧代-1H-4,5-二氢呋喃-3-羧酸衍生物氰乙酸衍生物
4. Ortho-Substituent Effect of Boronic Acid Catalysts on Direct Amide Condensation Reaction between Carboxylic Acids and Amines [C] . Ke Wang, Yanhui Lu, Kazuaki Ishihara 日本化学会春季年会講演予稿集 . 2018

机译：硼酸催化剂对羧酸和胺直接酰胺缩合反应的邻醇催化
5. Mechanistic Studies of Electrocatalytic Processes: Upgrading of Lignin Monomers to Biofuels (Probing Substrate Synergy); Alkylation of Amines with Alcohols Via Borrowing Hydrogen Mechanisms; and Reduction of the Carboxylic Acid Functionality in Amino Acid [D] . ?Appiagyei, Benjamin 2020

机译：电催化工艺的机械研究：将木质素单体升级到生物燃料（探测底物协同）; 通过借用氢机制烷基化胺与醇的烷基化; 并降低氨基酸中的羧酸官能团
6. Transition-metal-free decarboxylative bromination of aromatic carboxylic acids [O] . Jacob M. Quibell, Gregory J. P. Perry, Diego M. Cannas, 2018

机译：芳香族羧酸的无过渡金属脱羧溴化
7. Novel Regenerated Solvent Extraction Processes for the Recovery of Carboxylic Acids or Ammonia from Aqueous Solutions Part I. Regeneration of Amine-Carboxylic Acid Extracts [O] . Loree Joanne Poole, C. Judson King 1990

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8. Analyzing carboxylic acid and amine-nitro hydrogen-bond geometry in the cocrystal of 4-aminobenzoic acid and 3,5-dinitrobenzoic acid by use of 298 K X-ray and 15 K neutron diffraction [R] . Frankenbach, G. M., Etter, M. C., Schultz, A. J., 1993

机译：利用298 K X射线和15 K中子衍射分析4-氨基苯甲酸和3,5-二硝基苯甲酸共晶中的羧酸和胺 - 硝基氢键几何结构

Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids

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