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 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.

Automated summary

This report demonstrates a light-promoted water-mediated NBS photoinitiated cleavage method for electron-deficient conjugated alkenes under mild and greener conditions via the hydrogen atom transfer mechanism. Additionally, this methodology is shown to work as a deprotection step for carbonyl groups. The protocol exhibits wide range of functional group tolerance and high regioselectivity at room temperature in an aqueous medium.