N,N'-Carbonyldiimidazole-Mediated Amide Coupling: Significant Rate Enhancement Achieved by Acid Catalysis with Imidazole - HCl

Emily K. Woodman; Julian G. K. Chaffey; Philip A. Hopes

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N,N'-Carbonyldiimidazole-Mediated Amide Coupling: Significant Rate Enhancement Achieved by Acid Catalysis with Imidazole - HCl

机译：N，N'-羰基二咪唑介导的酰胺偶联：咪唑-HCl酸催化显着提高速率

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Over a series of 10 aromatic amines we show the rate of CDI mediated amidation to be significantly enhanced upon introduction of imidazole·HCl as a proton source for acid catalysis. Our work supports and provides an application for previous investigations into the imidazolium effect, thus increasing the scope of CDI as an amide-coupling reagent with aromatic amines. The influence of the relative pK_a of the amines studied on the rate of reaction was also investigated.

机译：在一系列10种芳香族胺上，我们显示了在引入咪唑·HCl作为质子酸催化源后，CDI介导的酰胺化反应速率显着提高。我们的工作支持并为以前的咪唑效应研究提供了应用，从而扩大了CDI作为与芳香胺的酰胺偶联剂的范围。还研究了胺的相对pK_a对反应速率的影响。

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《Organic process research & development》 |2009年第1期|共8页
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Emily K. Woodman; Julian G. K. Chaffey; Philip A. Hopes;
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1. N,N'-Carbonyldiimidazole-Mediated Amide Coupling: Significant Rate Enhancement Achieved by Acid Catalysis with Imidazole - HCl [J] . Emily K. Woodman, Julian G. K. Chaffey, Philip A. Hopes Organic process research & development . 2009,第1期

机译：N，N'-羰基二咪唑介导的酰胺偶联：咪唑-HCl酸催化显着提高速率
2. Decarbonylative Phosphorylation of Amides by Palladium and Nickel Catalysis: The Hirao Cross-Coupling of Amide Derivatives [J] . Liu Chengwei, Szostak Michal Angewandte Chemie . 2017,第41期

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3. Cul/amino acid catalysis in coupling and cyclization of β-bromo-α,β-unsaturated carboxylic acids with terminal alkynes leading to alkylidenefuranones [J] . Son Long Ho, Chan Sik Cho, Heung-Jin Choi Applied Organometallic Chemistry . 2013,第5期

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4. Towards Geochemically Accurate Modeling of Carbonate Acidizing with HCl Acid [C] . Mohamed Mahrous, Abdullah Sultan, Eric Sonnenthal SPE Annual Technical Conference and Exhibition . 2017

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5. 1. Reduction of Tertiary Benzamides to Benzaldehydes by an in situ-Generated Schwartz Reagent (Cp2 Zirconium (Hydrogen)Chloride); Formal Synthesis of Lysergic Acid. 2. Ru-Catalyzed Amide-Directed Aryl Carbon-Hydrogen, Carbon-Nitrogen and Carbon-Oxygen Bond Functionalizations: C-B Formation, Carbon-Carbon Suzuki Cross Coupling and Hydrodemethoxylation [D] . Zhao, Yigang 2011

机译：1.通过原位生成的Schwartz试剂（Cp2氯化锆（氢）氯化物）将叔苄酰胺还原为苯甲醛；麦角酸的正式合成。 2. Ru催化的酰胺基芳烃碳氢，碳氮和碳氧键功能化：C-B形成，碳-碳铃木交叉偶联和加氢脱甲氧基化
6. H-D exchange in deuterated trifluoroacetic acid via ligand-directed NHC-palladium catalysis: a powerful method for deuteration of aromatic ketones amides and amino acids [O] . Richard Giles, Green Ahn, Kyung Woon Jung -1

机译：通过配体定向的NHC-钯催化在氘代三氟乙酸中进行H-D交换：芳香族酮酰胺和氨基酸的氘代强大方法
7. H–D exchange in deuterated trifluoroacetic acid via ligand-directed NHC–palladium catalysis: a powerful method for deuteration of aromatic ketones, amides, and amino acids [O] . Richard Giles, Green Ahn, Kyung Woon Jung 2015

机译：通过配体定向的NHC-钯催化在氘代三氟乙酸中的H-D换算：芳香酮，酰胺和氨基酸氘的强大方法

N,N'-Carbonyldiimidazole-Mediated Amide Coupling: Significant Rate Enhancement Achieved by Acid Catalysis with Imidazole - HCl

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