Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates

Aryl sulfonate esters are versatile synthetic intermediates in organic chemistry as well as attractive architectures due to their bioactive properties. Herein, we report the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp(2))-C(sp(3)) cross-coupling of Grignard reagents with aryl chlorides. The method operates using an environmentally benign and sustainable iron catalytic system, employing benign urea ligands. A broad range of chlorobenzenesulfonates as well as challenging alkyl organometallics containing beta-hydrogens are compatible with these conditions, affording alkylated products in high to excellent yields. The study reveals that aryl sulfonate esters are the most reactive activating groups for iron-catalyzed alkylative C(sp(2))-C(sp(3)) cross-coupling of aryl chlorides with Grignard reagents.

Automated summary

Aryl sulfonate esters are versatile synthetic intermediates due to their bioactive properties. The study introduces a method for the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp(2))-C(sp(3)) cross-coupling, showing high reactivity and compatibility with a broad range of substrates. The environmentally benign and sustainable iron catalytic system plays a key role in achieving high to excellent yields of the alkylated products.