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硼氢化氮促进的深共熔溶剂中的硝基烯烃还原反应

Nitroalkene reduction in deep eutectic solvents promoted by BHNH.

作者信息

Faverio Chiara, Boselli Monica Fiorenza, Camarero Gonzalez Patricia, Puglisi Alessandra, Benaglia Maurizio

机构信息

Dipartimento di Chimica, Università degli Studi di Milano, Via C. Golgi, 19, I-20133, Milano, Italy.

出版信息

Beilstein J Org Chem. 2021 May 6;17:1041-1047. doi: 10.3762/bjoc.17.83. eCollection 2021.

DOI:10.3762/bjoc.17.83
PMID:34025809
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8111428/
Abstract

Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BHNH, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated.

摘要

深共熔溶剂(DESs)作为一种绿色、安全且经济环境可持续的传统有机溶剂替代品,已受到关注。在此,我们报道了将一种原子经济、非常便捷且廉价的试剂(如BHNH)与生物基共熔混合物作为生物可再生溶剂相结合,用于合成硝基烷烃(胺类的重要前体)。通过一种以原子经济性为导向、简单便捷的实验程序,多种硝基苯乙烯和烷基取代的硝基烯烃,包括α-和β-取代的硝基烯烃,被化学选择性还原为硝基烷烃。建立了一种可靠且易于重现的无需使用任何有机溶剂即可分离产物的方法,并成功研究了DES混合物的可循环利用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/0cfc8bba5661/Beilstein_J_Org_Chem-17-1041-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/bee76240b832/Beilstein_J_Org_Chem-17-1041-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/6ec4c0299d6e/Beilstein_J_Org_Chem-17-1041-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/6009b6e94027/Beilstein_J_Org_Chem-17-1041-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/0cfc8bba5661/Beilstein_J_Org_Chem-17-1041-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/bee76240b832/Beilstein_J_Org_Chem-17-1041-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/6ec4c0299d6e/Beilstein_J_Org_Chem-17-1041-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/6009b6e94027/Beilstein_J_Org_Chem-17-1041-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e80/8111428/0cfc8bba5661/Beilstein_J_Org_Chem-17-1041-g005.jpg

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