Micro-electro-flow catalyzed (μ-EFC) ultra-fast cross-electrophile coupling of activated C(sp)-O bonds

Over the past few decades, many batch process strategies have been developed that allow activated C(sp 3 )-O bonds to facilitate the synthesis of cross-electrophile coupling products. However, in these processes, a transition metal catalyst or an organic photocatalyst with a stoichiometric amount of...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-10, Vol.25 (21), p.8516-8523
Main Authors: Kumar, Sanjeev, Singh, Ajay K
Format: Article
Language:English
Subjects:
Aldehydes
Alkenes
Carbon dioxide
Carboxylic acids
Catalysts
Coupling
Deoxygenation
Gas-liquid reactions
Green chemistry
Ketones
Oxidants
Oxidizing agents
Reducing agents
Sulfonium salts
Transition metals
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Summary:Over the past few decades, many batch process strategies have been developed that allow activated C(sp 3 )-O bonds to facilitate the synthesis of cross-electrophile coupling products. However, in these processes, a transition metal catalyst or an organic photocatalyst with a stoichiometric amount of oxidant or a reductant is the prerequisite. Indeed, the expensive catalyst, reductant, and oxidant and low surface-to-volume ratio for the gas-liquid reaction serve as major challenges in the field of cross-electrophile coupling and organosulfur chemistry. Herein, we report an electro-micro-flow induced cross-electrophile coupling of activated C(sp 3 )-O bonds with CO 2 to generate aliphatic carboxylic acids via sequential reactions of sulfonium salts followed by replacement of CO 2 with CS 2 , an aldehyde, a ketone, and electron-deficient olefins, to obtain the corresponding dithiol acid, deoxygenated Barbier-type product, and 1,4-addition product. Herein, we reported electro-micro-flow induced carbanion generation, and subsequently quench with the various inactive electrophile such as CO 2 , CS 2 , an aldehyde, a ketone, and electron-deficient olefins, to obtain the corresponding product.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc03239f