Vitamin B<sub>12</sub> and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins

Vitamin B<sub>12</sub>, 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<sub>12</sub> 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<sub>12</sub> in sustainable catalysis providing a valuable method to synthesize important intermediates.

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Publication Details

Journal
Organic Letters
Published
2025-05-23
DOI
https://doi.org/10.1021/acs.orglett.5c01376
Citations
3
Primary Topic
Synthesis and Catalytic Reactions
Type
article
Field-Weighted Citation Impact
2.81

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article

Vitamin B12 and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins

Krzysztof Mazurek, Dorota Gryko, Tomasz Wdowik, Martin Andersson et al.
3 citations
Organic Letters
Synthesis and Catalytic Reactions
2.81
article

Vitamin B12 and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins

Krzysztof Mazurek, Dorota Gryko, Tomasz Wdowik, Martin Andersson, Kitti Franciska Szabó, Aleksandra Potrząsaj
article en
3 citations

Abstract

Vitamin B<sub>12</sub>, 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<sub>12</sub> 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<sub>12</sub> in sustainable catalysis providing a valuable method to synthesize important intermediates.

Organic LettersVol. 27(22)
King Fahd University of Petroleum and Minerals (SA), Institute of Organic Chemistry (PL), Polish Academy of Sciences (PL)
Narodowe Centrum Nauki
Zero hunger
Openalex Percentile: Top 10%
Synthesis and Catalytic Reactions
2.81
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