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Magnetically recoverable Ni@CuI hybrid nanocatalysts affording spiropyrroline heterocycles from ketoximes and alkenes
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-04-03 , DOI: 10.1002/ajoc.202000145 Upasana Gulati 1 , U. Chinna Rajesh 2 , Diwan S. Rawat 1
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-04-03 , DOI: 10.1002/ajoc.202000145 Upasana Gulati 1 , U. Chinna Rajesh 2 , Diwan S. Rawat 1
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The design of magnetic hybrid nanomaterials for cooperative activation of diverse functional groups drives future nanocatalysis toward green and sustainable multi‐component organic synthesis. Here, we report the synthesis of unique Ni@CuI hybrid nanocatalysts by oxidation of the Cu0 surface in Ni@Cu core‐shell precursor using an ethanolic I2 solution. The morphological (scanning electron microscopy and energy‐dispersive X‐ray spectroscopy) and structural (powder X‐ray diffraction and X‐ray photoelectron spectroscopy) characterizations conform the formation of Ni0 and CuI hybrid nanocatalysts. These are efficient catalysts for the activation of oxime and olefin substrates to afford spiropyrrolines in a short time and excellent yields under green reaction conditions. The control experiments delineate the role of Cu sites as redox (I–III) triggered cleavage of N−O bond (oximes) and Ni0 sites adsorb the olefin (C=C) which is proximity to the Cu‐enamide intermediate to enhance the intermolecular cyclization lead to spiropyrrolines. The robustness of Ni@CuI hybrid nanocatalyst is demonstrated over five cycles without loss in its turnover and structural integrity, which follows ideal green chemistry metrics.
中文翻译：
磁性可回收的Ni @ CuI杂化纳米催化剂，从酮肟和烯烃提供螺吡咯啉杂环
用于多种官能团协同活化的磁性杂化纳米材料的设计推动了未来的纳米催化朝着绿色和可持续的多组分有机合成方向发展。在这里，我们报告了通过使用乙醇I 2溶液氧化Ni @ Cu核壳前体中的Cu 0表面来合成独特的Ni @ CuI杂化纳米催化剂。形态学特征（扫描电子显微镜和能量色散X射线能谱）和结构特征（粉末X射线衍射和X射线光电子能谱）符合Ni 0的形成和CuI杂化纳米催化剂。这些是用于肟和烯烃底物活化的有效催化剂，可在绿色反应条件下在短时间内提供螺吡咯啉，并具有优异的收率。对照实验描述了铜位点的作用，因为氧化还原（I–III）触发了N-O键（肟）的裂解，而Ni 0位点吸附了接近铜烯酰胺中间体的烯烃（C = C），从而增强了分子间环化导致螺吡咯啉。在五个循环中证明了Ni @ CuI杂化纳米催化剂的稳健性，没有损失其周转率和结构完整性，这符合理想的绿色化学指标。
更新日期：2020-04-03
中文翻译：
磁性可回收的Ni @ CuI杂化纳米催化剂，从酮肟和烯烃提供螺吡咯啉杂环
用于多种官能团协同活化的磁性杂化纳米材料的设计推动了未来的纳米催化朝着绿色和可持续的多组分有机合成方向发展。在这里，我们报告了通过使用乙醇I 2溶液氧化Ni @ Cu核壳前体中的Cu 0表面来合成独特的Ni @ CuI杂化纳米催化剂。形态学特征（扫描电子显微镜和能量色散X射线能谱）和结构特征（粉末X射线衍射和X射线光电子能谱）符合Ni 0的形成和CuI杂化纳米催化剂。这些是用于肟和烯烃底物活化的有效催化剂，可在绿色反应条件下在短时间内提供螺吡咯啉，并具有优异的收率。对照实验描述了铜位点的作用，因为氧化还原（I–III）触发了N-O键（肟）的裂解，而Ni 0位点吸附了接近铜烯酰胺中间体的烯烃（C = C），从而增强了分子间环化导致螺吡咯啉。在五个循环中证明了Ni @ CuI杂化纳米催化剂的稳健性，没有损失其周转率和结构完整性，这符合理想的绿色化学指标。
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