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Synthesis of Thieno[3,2‑b]indoles via Halogen Dance and Ligand-Controlled One-Pot Sequential Coupling Reaction

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journal contribution
posted on 08.02.2018, 17:05 by Yuki Hayashi, Kentaro Okano, Atsunori Mori
A two-pot synthesis of thieno­[3,2-b]­indole from 2,5-dibromothiophene is described. A halogen dance of 2,5-dibromothiophene was performed with LDA, and subsequent Negishi coupling was performed with 2-iodoaniline derivatives to provide the corresponding coupling products. The resulting two bromo groups have different reactivities, which were utilized for the one-pot Suzuki–Miyaura coupling/intramolecular Buchwald–Hartwig amination to produce thieno­[3,2-b]­indole via an assisted tandem catalysis that involved in situ ligand exchange.