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Aqueous Micellar Environment Impacts the Co-Catalyzed Phototransformation: A Case Study

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Journal J Am Chem Soc
Specialty Chemistry
Date 2024 Jul 14
PMID 39003762
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Abstract

In recent years, methodologies that rely on water as the reaction medium have gained considerable attention. The unique properties of micellar solutions were shown to improve the regio-, stereo-, and chemoselectivity of different transformations. Herein, we demonstrate that the aqueous environment is a suitable medium for a visible light driven cobalt-catalyzed reaction involving radical species. In this system, reduced vitamin B reacts with alkyl halides, generating radicals that are trapped by the lipophilic olefin present in the Stern layer. A series of NMR measurements and theoretical studies revealed the location of reaction components in the micellar system.

References
1.
Mannel-Croise C, Zelder F . Immobilised vitamin B12 as a biomimetic model for base-off/histidine-on coordination. Chem Commun (Camb). 2011; 47(40):11249-51. DOI: 10.1039/c1cc15093f. View

2.
Andruniow T, Zgierski M, Kozlowski P . Theoretical determination of the Co-C bond energy dissociation in cobalamins. J Am Chem Soc. 2001; 123(11):2679-80. DOI: 10.1021/ja0041728. View

3.
Zhu C, Ang N, Meyer T, Qiu Y, Ackermann L . Organic Electrochemistry: Molecular Syntheses with Potential. ACS Cent Sci. 2021; 7(3):415-431. PMC: 8006177. DOI: 10.1021/acscentsci.0c01532. View

4.
Potrzasaj A, Musiejuk M, Chaladaj W, Giedyk M, Gryko D . Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides. J Am Chem Soc. 2021; 143(25):9368-9376. PMC: 8297733. DOI: 10.1021/jacs.1c00659. View

5.
Kitanosono T, Kobayashi S . Reactions in Water Involving the "On-Water" Mechanism. Chemistry. 2020; 26(43):9408-9429. DOI: 10.1002/chem.201905482. View