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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.

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/bcf18a385649/ol5c01376_0002.jpg

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