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Rhodium-Catalyzed Intramolecular Acylation of 2-(Indol-1-yl)benzoic Acids under Redox-Neutral Conditions

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We developed a novel access to indoloindolone by a rhodium-catalyzed intramolecular acylation of 2-(indol-1-yl)benzoic acids. This reaction proceeds via the in situ formation of a mixed anhydride under redox-neutral reaction… Click to show full abstract

We developed a novel access to indoloindolone by a rhodium-catalyzed intramolecular acylation of 2-(indol-1-yl)benzoic acids. This reaction proceeds via the in situ formation of a mixed anhydride under redox-neutral reaction conditions. Preliminary mechanistic investigations revealed that the in situ-formed mixed anhydride participates in the C–H activation step, which is facilitated by a RhI catalyst. The utility of this reaction was demonstrated by a large-scale reaction.

Keywords: catalyzed intramolecular; indol benzoic; intramolecular acylation; rhodium catalyzed; acylation indol; benzoic acids

Journal Title: Synlett
Year Published: 2023

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