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Highly efficient aluminum-catalyzed hydro-amination/-hydrazination of carbodiimides

机译：碳二亚胺的高效铝催化加氢胺化/肼化

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摘要

The catalytic activity of commercially available [Al(NMe_2) _3]_2 (1) and a dimethyl aluminum guanidinate complex toward the hydro-amination/-hydrazination of carbodiimides was studied. The guanidinate-supported complex 2 was prepared via salt metathesis reactions of AlMe_2Cl and an in situ generated lithium guanidinate reagent. X-ray crystallographic studies revealed the influence of the guanidinate ligand on the Al metal center. Hydroamination reactions were successfully carried out at room temperature with 2 as the catalyst, while 1 proved to be ineffective under these conditions. On the contrary, both 1 and 2 were active toward the hydro-hydrazination of carbodiimides, which were run at elevated temperatures (120 °C). Consequently, the reaction temperature had a significant influence on the choice of the catalyst since the catalytically active species can be generated from various precatalysts under different conditions. The formation of guanidines and aminoguanidines showed a high functional group tolerance and typically proceeded with excellent yields at low catalyst loadings. X-ray crystallographic studies of compound 4a revealed interesting structural features of the previously unknown aminoguanidine products. The independently isolated Al aminoguanidinate complex 5 showed catalytic activity toward hydro-hydrazination chemistry and provided valuable evidence in support of the proposed reaction mechanism.
机译：研究了市售的[Al（NMe_2）_3] _2（1）和胍基二甲基铝配合物对碳二亚胺的加氢胺化/酰化反应的催化活性。通过AlMe_2Cl与原位生成的胍基锂试剂的盐复分解反应制备了胍基负载的配合物2。 X射线晶体学研究表明胍盐配体对Al金属中心的影响。在室温下以2为催化剂成功进行了加氢胺化反应，而在这些条件下1证明是无效的。相反，1和2均对碳化二亚胺的加氢酰肼反应有活性，碳化二亚胺在高温（120°C）下进行。因此，反应温度对催化剂的选择有重要影响，因为催化活性物质可以在不同条件下由各种预催化剂产生。胍和氨基胍的形成显示出高的官能团耐受性，并且通常在低催化剂负载下以优异的产率进行。化合物4a的X射线晶体学研究显示了以前未知的氨基胍产物的有趣结构特征。独立分离的铝氨基胍盐配合物5对氢酰化化学具有催化活性，并为支持所提出的反应机理提供了有价值的证据。

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