Synthetic study demonstrates selective ortho-directed C–H borylation of simple nitroarenes via an iridium catalyst, enabling streamlined synthesis of functionalized arenes.
Abstract ortho-Boryl nitroarenes have vast applications as building blocks in organic synthesis. Traditional methods of synthesizing these compounds require an ortho-halo nitroarene starting material and often stringent conditions. Directed ortho-borylation of nitroarenes presents an alternative, attractive strategy that could utilize simple nitroarenes as a feedstock. Herein, we report a cationic iridium pre-catalyst and triarylarsine ligands as competent catalyst systems that selectively borylate nitroarenes at the ortho position. This nitro-directed C–H borylation tolerates a wide range of substrates, providing access to diverse ortho-boryl nitroarenes in high yields that can either be isolated directly or reacted without purification to provide functionalized nitroarenes. Finally, we also demonstrate that ortho-boryl nitroarenes can serve as a platform for the synthesis of diverse aromatic products, including the preparation of 1,2-difunctionalized arenes.
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Idowu et al. (2026) studied this question.
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