Synthesis of Sterically Congested Carbonyl Compounds via an ipso-Selective Sulfonium Rearrangement

Abstract

Despite the success of metal-catalyzed cross-coupling strategies to assemble a variety of C–C bonds, the synthesis of sterically congested α-arylated carbonyl compounds remains a difficult task. Herein, we present an ipso-rearrangement approach relying on electron redistribution in sulfonium intermediates. This modular method enables the synthesis of a variety of α-arylated carbonyl compounds and is orthogonal to traditional metal-catalyzed cross-coupling strategies. More importantly, it demonstrated remarkable robustness toward steric hindrance and allowed us to efficiently forge congested C–C bonds.