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Catalytic Room-Temperature C-N Coupling of Amides and Isocyanates by Using Mechanochemistry.
ChemSusChem ( IF 8.4 ) Pub Date : 2020-03-28 , DOI: 10.1002/cssc.201902576
Gandrath Dayaker 1 , Davin Tan 1 , Naomi Biggins 1 , Asha Shelam 1 , Jean-Louis Do 1 , Athanassios D Katsenis 1 , Tomislav Friščić 1
Affiliation  

A mechanochemical route is developed for room‐temperature and solvent‐free derivatization of different types of amides into carbamoyl isatins (up to 96 % conversion or yield), benzamides (up to 81 % yield), and imides (up to 92 % yield). In solution, this copper‐catalyzed coupling either does not take place or requires high temperatures at which it may also be competing with alternative thermal reactivity, highlighting the beneficial role of mechanochemistry for this reaction. Such behavior resembles the previously investigated coupling with sulfonamide substrates, suggesting that this type of C−N coupling is an example of a mechanochemically favored reaction, for which mechanochemistry appears to be a favored environment over solution.

中文翻译:

利用机械化学催化酰胺和异氰酸酯的室温室温CN偶联。

已开发出一种机械化学路线,可将不同类型的酰胺在室温和无溶剂条件下衍生为氨基甲酰基isatins(转化率或产率高达96%),苯甲酰胺(产率高达81%)和酰亚胺(产率高达92%) 。在溶液中,这种铜催化的偶联反应要么不发生,要么需要高温,在高温下它也可能与其他的热反应性竞争,从而突出了机械化学对该反应的有益作用。这种行为类似于先前研究的与磺酰胺底物的偶联,表明这种C-N偶联是机械化学上有利的反应的一个例子,对于该化学反应,机械化学似乎是比溶液更有利的环境。
更新日期:2020-03-28
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