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September 16, 2025Open Access

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

RJRita de JesusKiel University JDJyotirmoy DeyKiel University ECElisa ChakrabortyCentre National de la Recherche Scientifique

Key Points

Nondirected C(sp2)-H carboxylation and formylation yield diverse regioisomeric products from arenes, enhancing synthesis.
By utilizing a dual ligand-based catalyst, over previously inaccessible positions, predictable regioselectivity is accomplished.
The method combines nondirected olefination with oxidative cleavage, demonstrating broad scope and synthetic utility.
This approach supports late-stage functionalization, allowing for the incorporation of complex motifs into diverse compounds.

Abstract

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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