Deconstruction of electron-deficient alkenes to carbonyl constituents by light-induced hydrogen atom transfer

Deconstruction of alkenes to their carbonyl derivatives is a widely used protocol in synthetic organic chemistry and several reaction conditions have been demonstrated for electron-rich and unconjugated alkenes. However, such reactions of electron-deficient and conjugated alkenes are highly challeng...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-02, Vol.25 (3), p.178-184
Main Authors: Das, Anupam, Justin Thomas, K. R
Format: Article
Language:English
Subjects:
Alkenes
Aqueous solutions
Carbonyl compounds
Carbonyl groups
Carbonyls
Functional groups
Green chemistry
Hydrogen atoms
Light effects
Organic chemistry
Regioselectivity
Room temperature
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Summary:Deconstruction of alkenes to their carbonyl derivatives is a widely used protocol in synthetic organic chemistry and several reaction conditions have been demonstrated for electron-rich and unconjugated alkenes. However, such reactions of electron-deficient and conjugated alkenes are highly challenging. In this report, we have demonstrated a light-promoted water-mediated NBS photoinitiated cleavage of electron-deficient conjugated alkenes under mild and greener conditions via the hydrogen atom transfer mechanism. Additionally, this methodology is demonstrated as a deprotection step for carbonyl groups. This protocol works at room temperature in an aqueous medium with a wide range of functional group tolerance and high regioselectivity. Photoinduced C&z.dbd;C bond cleavage by the HAT mechanism: photoinitiated catalyst-free C&z.dbd;C bond cleavage for the regeneration of carbonyl compounds from electron-deficient conjugated alkenes is developed as a deprotection strategy in an aqueous medium.
ISSN:1463-9262
1463-9270
DOI:10.1039/d2gc04424b