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Facile access to amino-substituted cyclopentafullerenes: novel reaction of [60]fullerene with β-substituted propionaldehydes and secondary amines in the absence/presence of magnesium perchlorate.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-08-19 , DOI: 10.1039/d0ob00008f Yun-Fei Li 1 , Kun Wang , Hui-Juan Wang , Fa-Bao Li , Rui Sun , Jia-Xing Li , Li Liu , Chao-Yang Liu , Abdullah M Asiri
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-08-19 , DOI: 10.1039/d0ob00008f Yun-Fei Li 1 , Kun Wang , Hui-Juan Wang , Fa-Bao Li , Rui Sun , Jia-Xing Li , Li Liu , Chao-Yang Liu , Abdullah M Asiri
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A series of scarce amino-substituted cyclopentafullerenes instead of the expected N-alkyl-2,5-disubstituted fulleropyrrolidines were synthesized in moderate to excellent yields via the simple one-step reaction of [60]fullerene with cheap and easily available β-substituted propionaldehydes and secondary amines in the absence/presence of magnesium perchlorate. The in situ generation of allylic amines from β-substituted propionaldehydes and secondary amines played a crucial role in the successful preparation of amino-substituted cyclopentafullerenes without additional carbons. With the addition of magnesium perchlorate, secondary amines containing ethyl group(s) could produce novel amino-substituted cyclopentafullerenes with two additional carbons. All the obtained cyclopentafullerenes displayed high stereoselectivity with cis isomers as the exclusive or major products. Plausible reaction mechanisms are proposed to elucidate the above-mentioned reaction process.
中文翻译：
容易获得氨基取代的环戊富勒烯：在高氯酸镁不存在/存在的情况下，[60]富勒烯与β-取代的丙醛和仲胺的新反应。
通过[60]富勒烯与廉价且易于获得的β-取代丙醛的简单一步反应，以中等至优异的产率合成了一系列稀有的氨基取代的环戊富勒烯，而不是预期的N-烷基-2,5-二取代的富勒吡咯烷和仲胺在不存在/存在高氯酸镁的情况下。现场的从β-取代的丙醛和仲胺生成烯丙基胺在成功制备不含额外碳的氨基取代的环戊富勒烯中发挥了关键作用。添加高氯酸镁后，含有乙基的仲胺可以产生具有两个额外碳的新型氨基取代的环戊富勒烯。所有获得的环戊富勒烯均表现出高立体选择性，顺式异构体为唯一或主要产物。提出了合理的反应机制来阐明上述反应过程。
更新日期：2020-09-16
中文翻译：
容易获得氨基取代的环戊富勒烯：在高氯酸镁不存在/存在的情况下，[60]富勒烯与β-取代的丙醛和仲胺的新反应。
通过[60]富勒烯与廉价且易于获得的β-取代丙醛的简单一步反应，以中等至优异的产率合成了一系列稀有的氨基取代的环戊富勒烯，而不是预期的N-烷基-2,5-二取代的富勒吡咯烷和仲胺在不存在/存在高氯酸镁的情况下。现场的从β-取代的丙醛和仲胺生成烯丙基胺在成功制备不含额外碳的氨基取代的环戊富勒烯中发挥了关键作用。添加高氯酸镁后，含有乙基的仲胺可以产生具有两个额外碳的新型氨基取代的环戊富勒烯。所有获得的环戊富勒烯均表现出高立体选择性，顺式异构体为唯一或主要产物。提出了合理的反应机制来阐明上述反应过程。
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