Iron-Catalyzed Sodium Iodide-Promoted Aerobic Oxidative Cross-Coupling of Benzofurans with Indoles
Angulimal Kamble1, Shon Gangai1, Rishikesh Narayan1,2
1School of Chemical & Materials Sciences (SCMS), Indian Institute of Technology Goa, Farmagudi, Goa403401, India.
Abstract:
Benzofuran-indole heterobiaryls are important structural motifs with widespread applications. However, their synthesis is limited to methods requiring Pd catalysts and prefunctionalized substrates. Herein, we report the first general oxidative cross-coupling of benzofurans with indoles under aerobic, Fe(III)-catalyzed conditions with NaI as a catalytic promoter. The reaction displays wide substrate scope and high chemo- and regioselectivity. Preliminary mechanistic experiments indicate a single-electron-transfer (SET)-based mechanism with radical cation-nucleophile coupling as the crucial bond-forming step.
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