2025/09/15 by Rita de Jesus, Jyotirmoy Dey, Elisa Chakraborty +1 · 1 voice · 2 citations
Chemistry · #Catalytic C–H Functionalization Methods #Oxidative Organic Chemistry Reactions #Synthesis and Catalytic Reactions
paper · pdf · doi:10.1021/acs.orglett.5c03474
High Resolution Image Download MS PowerPoint Slide Carboxyl- and formyl-substituted arenes are key motifs in organic chemistry, typically prepared via electrophilic aromatic substitution (S E Ar) reactions. S E Ar 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(sp 2 )–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.