Palladium catalysis in the intramolecular carbene C-H insertion of α-diazo-α-(methoxycarbonyl)acetamides to form β-lactams,European Journal of Organic Chemistry

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Palladium catalysis in the intramolecular carbene C-H insertion of α-diazo-α-(methoxycarbonyl)acetamides to form β-lactams
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2018-08-13 , DOI: 10.1002/ejoc.201800666
Daniel Solé ₁ , Ferran Pérez-Janer ₁ , M.-Lluïsa Bennasar ₁ , Israel Fernández ₂

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The intramolecular carbene C–H insertion of α-diazo-α(methoxycarbonyl)acetamides leading to β-lactams is effectively catalyzed by palladium complexes. It is found that whereas Pd(0)catalysts typically produce mixtures of β-lactams together with Buchner-type reaction products, the use of Pd(II)-catalysts results in highly chemoselective transformations. According to DFT calculations, this insertion reaction occurs stepwise and involves an unprecedented Pd(II)-promoted Mannich-type reaction through a metallacarbene-induced zwitterionic intermediate.

中文翻译：

钯催化α-重氮-α-(甲氧基羰基)乙酰胺分子内卡宾CH插入形成β-内酰胺

钯配合物有效催化α-重氮-α（甲氧基羰基）乙酰胺的分子内卡宾C-H插入生成β-内酰胺。发现 Pd(0) 催化剂通常产生 β-内酰胺与 Buchner 型反应产物的混合物，而 Pd(II) 催化剂的使用导致高度化学选择性转化。根据 DFT 计算，这种插入反应是逐步发生的，并且涉及前所未有的 Pd(II) 促进的曼尼希型反应，通过金属碳烯诱导的两性离子中间体。

更新日期：2018-08-13

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