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 beta-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 beta-position and a C-I bond at its beta-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 alpha-selective carboiodoination. To demonstrate the developed methodology's potential, synthetic transformations were also performed, starting from the generated carboiodinated products.