Regioselective Carboiodination of Styrenes: N ‐Iodosuccinimide Affords Complete Reaction Regioselectivity

In organic synthesis, the regioselective bifunctionalization of olefins remains an unmet challenge. In this study, the cationic iodine‐mediated complete β‐selective carboiodoination of styrene and styrene‐like compounds with Meldrum's acid was achieved. The reaction, thus developed, proceeded with the formation of a C−C bond at the olefin's β‐position and a C−I bond at its β‐position, via a single‐step reaction between Meldrum's acid and an iodonium intermediate. The developed strategy suppresses the formation of undesired side‐reactions, resulting from α‐selective carboiodoination. To demonstrate the developed methodology's potential, synthetic transformations were also performed, starting from the generated carboiodinated products.