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Triazene as the Directing Group Achieving Highly Ortho-Selective Diborylation and Sequential Functionalization.

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This study describes a regioselective ortho,ortho'-diborylation of aromatic triazenes catalyzed by [Ir(OMe)(cod)]2 in near-quantitative yields without an additional ligand. Aromatic triazenes act as both substrates and ligands. The X-ray structures… Click to show full abstract

This study describes a regioselective ortho,ortho'-diborylation of aromatic triazenes catalyzed by [Ir(OMe)(cod)]2 in near-quantitative yields without an additional ligand. Aromatic triazenes act as both substrates and ligands. The X-ray structures of 2a and 2p indicate that the monoborylation products could promote the occurrence of diborylation. The synthesized triazene-substituted diboronate esters could undergo a variety of transformations including directing group removal. One-pot sequential modification provides a short entry to densely functionalized arenes.

Keywords: group achieving; diborylation; triazene directing; achieving highly; directing group

Journal Title: Organic letters
Year Published: 2022

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