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维生素B与胶束溶液可实现环氧化物和氮丙啶与亲电烯烃的区域选择性开环反应。

Vitamin B and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins.

作者信息

Szabó Kitti Franciska, Wdowik Tomasz, Krzeszewska Aleksandra, Mazurek Krzysztof, Andersson Martin P, Gryko Dorota

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

Center for Integrative Petroleum Research, King Fahd University of Petroleum and Minerals, Dhahran 31261, Kingdom of Saudi Arabia.

出版信息

Org Lett. 2025 Jun 6;27(22):5642-5646. doi: 10.1021/acs.orglett.5c01376. Epub 2025 May 23.

DOI:10.1021/acs.orglett.5c01376
PMID:40408636
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12150321/
Abstract

Vitamin B, a water-soluble cobalt complex, is inherently predisposed to catalyze reactions under aqueous conditions. Despite its potential, adopting this strategy for transformations of hydrophobic reagents has been challenging, because of their low aqueous solubility. Here, we demonstrate that vitamin B promotes the reaction of epoxides and aziridines with electrophilic olefins in a micellar system. The desired products are obtained efficiently in a fully regioselective manner. This green catalytic approach further advances the use of vitamin B in sustainable catalysis providing a valuable method to synthesize important intermediates.

摘要

维生素B是一种水溶性钴配合物，本质上易于在水性条件下催化反应。尽管有其潜力，但由于疏水试剂在水中的溶解度低，采用这种策略进行疏水试剂的转化一直具有挑战性。在这里，我们证明了维生素B在胶束体系中促进环氧化物和氮丙啶与亲电烯烃的反应。以完全区域选择性的方式高效地获得了所需产物。这种绿色催化方法进一步推动了维生素B在可持续催化中的应用，为合成重要中间体提供了一种有价值的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b710/12150321/5ab1024e1ee0/ol5c01376_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b710/12150321/bcf18a385649/ol5c01376_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b710/12150321/abc11809caf7/ol5c01376_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b710/12150321/5ab1024e1ee0/ol5c01376_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b710/12150321/bcf18a385649/ol5c01376_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b710/12150321/abc11809caf7/ol5c01376_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b710/12150321/5ab1024e1ee0/ol5c01376_0001.jpg

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本文引用的文献

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J Am Chem Soc. 2024 Jul 24;146(29):19828-19838. doi: 10.1021/jacs.4c02682. Epub 2024 Jul 9.
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Photochemical cyclopropanation in aqueous micellar media - experimental and theoretical studies.水相胶束介质中的光化学环丙烷化反应——实验与理论研究
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Vitamin B and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening.
维生素B与氢原子转移协同催化作为环氧化物开环中氢化物亲核试剂的模拟物
Cell Rep Phys Sci. 2023 Apr 19;4(4). doi: 10.1016/j.xcrp.2023.101372. Epub 2023 Apr 12.
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Ni/Photoredox-Catalyzed C(sp)-C(sp) Coupling between Aziridines and Acetals as Alcohol-Derived Alkyl Radical Precursors.镍/光氧化还原催化氮丙啶和缩醛之间的 C(sp)-C(sp)偶联反应作为醇衍生的烷基自由基前体。
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Epoxides: Small Rings to Play with under Asymmetric Organocatalysis.环氧化合物：不对称有机催化作用下可用于研究的小环化合物
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Single-Micelle and Single-Zinc-Particle Imaging Provides Insights into the Physical Processes Underpinning Organozinc Reactions in Water.单胶束和单锌粒子成像为揭示水相有机锌反应的物理过程提供了新视角。
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