Sterically Controlled C(sp2)-H Carboxylation and Formylation: A Complementary Strategy to SEAr Approaches

Carboxyl- and formyl-substituted arenes are key motifs in organic chemistry, typically prepared via electrophilic aromatic substitution (SEAr) reactions. SEAr reactions hold tremendous synthetic value, and one of the key advantages is their predictable regioselectivity. Conversely, certain positions remain out of reach, such as sterically accessible but comparably electron-poor sites. Herein, we describe a nondirected C(sp2)-H carboxylation and formylation of arenes enabled by a dual ligand-based catalyst. By optimizing the steric control of a nondirected olefination of arenes and combining this method with two distinct protocols for the subsequent oxidative cleavage of alkenes, we can generate a complementary set of regioisomeric products. The synthetic utility is demonstrated by a broad scope with suitability for late-stage functionalization.

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