Chemical synthesis study demonstrates redox-neutral vicinal dialkylation of aryl boronic esters, highlighting streamlined pathways for assembling complex benzoazepanes.
Palladium/norbornene (Pd/NBE) cooperative catalysis has become an increasingly important tool for ipso/ortho difunctionalization of arenes; however, the ipso functionalization is primarily limited to coupling of a nucleophile or a π-system. Here, we report a new type of Pd/NBE-catalyzed difunctionalization reaction that simultaneously couples two alkyl electrophiles at the ipso and ortho positions of arenes. Diverse aryl boronic esters are employed as substrates. The redox-neutral feature of this reaction allows broad functional group tolerance. The synthetic utility is demonstrated in a streamlined preparation of a complex benzoazepane. Mechanistic studies reveal the potential involvement of an unusual radical-mediated ipso functionalization.
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Ye et al. (2026) studied this question.
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