Radical Bifunctionalization of Alkenes with Arylsulfonylacetate as Bifunctional Reagent via Photoredox Radical Addition/Smiles Rearrangement Cascade

02 January 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


We present herein a modular photoredox strategy for the difunctionalization of alkenes employing arylsulfonyl acetate as the bifunctional reagents. Under photoredox conditions, the electrophilic carbon-centered radical, generated from bifunctional reagent, add to alkenes followed by 1,4-aryltranlocation, providing a robust alternative to synthetic valuable γ,γ-diaryl and γ-aryl ester compounds. This method features mild reaction conditions, high atom- and step- economy, excellent functional group compatibility and great structural diversity. A complementary oxidative bifunctional reagents activation mode governs the radical cascade reactions, facilitating the simultaneous incorporation of aryl and carboxylate bearing alkyl groups into the alkenes.


Smiles Rearrangement
bifunctional reagent


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.