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研究绿色溶剂和无溶剂条件在氢键介导的有机催化模型反应中的功效。

Investigating the efficacy of green solvents and solvent-free conditions in hydrogen-bonding mediated organocatalyzed model reactions.

作者信息

Chetty Lloyd C, Kruger Hendrik G, Arvidsson Per I, Naicker Tricia, Govender Thavendran

机构信息

Catalysis and Peptide Research Unit, University of KwaZulu Natal Durban 4001 South Africa.

Science for Life Laboratory, Drug Discovery & Development Platform & Division of Translational Medicine and Chemical Biology, Department of Medical Biochemistry and Biophysics, Karolinska Institutet Stockholm Sweden.

出版信息

RSC Adv. 2024 Mar 7;14(12):7992-7998. doi: 10.1039/d4ra00679h. eCollection 2024 Mar 6.

DOI:10.1039/d4ra00679h
PMID:38454950
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10918449/
Abstract

In this study, we have delved into various reactions conducted using green solvents or under solvent-free conditions, employing hydrogen bonding organocatalysis to advance more sustainable practices in chemical synthesis. The outcomes suggest that cyclopentyl methyl ether could potentially replace non-polar organic solvents such as hexane and toluene with comparable enantioselectivity and yields. The non-polar nature of liquefied or supercritical CO restricts its application to reactions that require non-polar solvents. Furthermore, pursuing solvent-free conditions, even without liquid substrates, might result in similar conversion rates with reduced catalyst loading. These findings highlight the potential of exploring solvent-free conditions when enantioselectivity is not of concern. Based on the results, solvent-free conditions and bio-based solvents can serve as viable alternatives to conventional organic solvents without compromising performance. This is expected to influence the way chemists approach reaction optimisation within method development in the field, fostering a broader adoption of environmentally friendly approaches.

摘要

在本研究中,我们深入探讨了使用绿色溶剂或在无溶剂条件下进行的各种反应,采用氢键有机催化来推动化学合成中更具可持续性的实践。结果表明,环戊基甲基醚有可能以相当的对映选择性和产率替代己烷和甲苯等非极性有机溶剂。液化或超临界CO₂的非极性性质限制了其在需要非极性溶剂的反应中的应用。此外,即使没有液体底物,追求无溶剂条件也可能在降低催化剂负载量的情况下实现相似的转化率。这些发现突出了在对映选择性无关紧要时探索无溶剂条件的潜力。基于这些结果,无溶剂条件和生物基溶剂可以作为传统有机溶剂的可行替代品,而不会影响性能。这有望影响化学家在该领域方法开发中进行反应优化的方式,促进更广泛地采用环保方法。