Issue 3, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Nov 2022
Accepted
06 Jan 2023
First published
11 Jan 2023

Green Chem., 2023,25, 1078-1084

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

A. Das and K. R. Justin Thomas, Green Chem., 2023, 25, 1078 DOI: 10.1039/D2GC04424B

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