Vitamin B12 and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening

Funk, Brian E.; Pauze, Martin; Lu, Yen-Chu; Moser, Austin J.; Wolf, Gemma; West, Julian G.

doi:10.1016/j.xcrp.2023.101372

Cited by 4 publications

(1 citation statement)

References 29 publications

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“…In April 2023, our group discovered a mild epoxide reduction, utilizing VB 12 and 2,4,6‐triisopropylbenzene‐thiol (TRIP Thiol) in cooperative catalysis (Figure 5). [24] Following an analogous epoxide opening/homolysis sequence as employed by Gryko, we envisioned introducing a cooperative HAT cycle using TRIP thiol to deliver a hydrogen atom to the terminal radical, forming a Markovnikov alcohol selectively, a result in contrast to titanium‐based radical reduction methods [23d] . Fortuitously, both the thiyl radical and Co(II) intermediates are able to be reduced by a common reducing system, allowing for the entire reduction reaction to be driven by Zn/NH 4 Cl in methanol.…”

Section: Regioselective Reduction Of Epoxides Using Cooperative Vb12 ...mentioning

confidence: 99%

Vitamin B₁₂ in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis

Moser,

Funk,

West

2024

ChemCatChem

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Vitamin B12 (VB12) is a flexible and sustainable catalyst both in nature and the reaction flask, facilitating varied organic transformations of high value to both enzymatic processes and synthetic chemists. Key to this value is the breadth of reactivity it possesses, capable of both ionic, 2 electron chemistry, and radical, 1 electron chemistry. In particular, the ability to generate carbon‐centered radical intermediates via photolysis of organocobalt intermediates formed from alkyl electrophiles opens the door to powerful new radical transformations challenging to achieve using classical photoredox or ligand‐to‐metal charge transfer (LMCT) catalysis. While this unique photocatalytic reactivity of VB12 has been increasingly leveraged in monocatalytic schemes, recent reports have demonstrated VB12 is able to function as a powerful photocatalyst in cooperative schemes, driving diverse reactivity including remote elimination of alkyl halides, regioselective epoxide arylation, and regioselective epoxide reduction. This concept briefly overviews the enabling properties of VB12 as a photocatalyst and recent applications in cooperative catalysis, providing a framework for the continued development of new cooperative catalyst systems using this powerful photoactive complex.

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Section: Regioselective Reduction Of Epoxides Using Cooperative Vb12 ...mentioning

confidence: 99%

Vitamin B₁₂ in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis

Moser,

Funk,

West

2024

ChemCatChem

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Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art

Furniel,

Corrêa

2024

ChemPhotoChem

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The development of greener methods for the preparation of three‐membered rings has increased in the last decade, not only due to their biological activity, but also by the ring strain of those heterocycles that make them useful precursors of more complex molecules. In this work, the visible‐light‐promoted synthesis and ring‐opening of aziridines and epoxides, reported in the last five years, were reviewed. Both homogeneous and heterogeneous catalysts were discussed and, in addition, the plausible mechanism pathways were highlighted.

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Building Catalytic Reactions One Electron at a Time

West

2024

Acc. Chem. Res.

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Vitamin B12 and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening

Cited by 4 publications

References 29 publications

Vitamin B₁₂ in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis

Vitamin B₁₂ in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis

Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art

Building Catalytic Reactions One Electron at a Time

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Vitamin B12 and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening

Cited by 4 publications

References 29 publications

Vitamin B12 in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis

Vitamin B12 in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis

Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art

Building Catalytic Reactions One Electron at a Time

Contact Info

Product

Resources

About

Vitamin B₁₂ in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis

Vitamin B₁₂ in Photocatalysis – An Underexplored Frontier in Cooperative Catalysis