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Synthesis of Substituted Benzo[b]thiophenes via Sequential One-Pot, Copper-Catalyzed Intermolecular C-S Bond Formation and Palladium-Catalyzed Intramolecular Arene-Alkene Coupling of Bis(het)aryl/alkyl-1,3-monothiodiketones and o-Bromoiodoarenes



Synthesis of Substituted Benzo[b]thiophenes via Sequential One-Pot, Copper-Catalyzed Intermolecular C-S Bond Formation and Palladium-Catalyzed Intramolecular Arene-Alkene Coupling of Bis(het)aryl/alkyl-1,3-monothiodiketones and o-Bromoiodoarenes



Organic Letters 19(7): 1512-1515



A new, convergent, one-pot synthesis of 2,3-substituted benzo[b]thiophenes from readily available 1,3-bis(het)aryl-1,3-monothiodiketones and o-bromoiodoarenes involving a sequential copper-catalyzed intermolecular C-S coupling followed by palladium-catalyzed intramolecular arene-alkene coupling of in situ generated β-(o-bromoaryl)thiovinylketones has been described. Synthesis of a few thieno- and furano-fused 2-(het)aroylethylidenethiochromenes via intramolcular direct C-H (het)arylation of β-(o-bromoaryl)thioenones carrying 2-thienyl/furyl groups under different palladium-catalyzed conditions has also been reported.

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Accession: 060309533

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PMID: 28299938

DOI: 10.1021/acs.orglett.7b00273


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