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  • Title: One-pot synthesis of functionalized benzo[b]thiophenes and their hetero-fused analogues via intramolecular copper-catalyzed S-arylation of in situ generated enethiolates.
    Author: Acharya A, Vijay Kumar S, Saraiah B, Ila H.
    Journal: J Org Chem; 2015 Mar 06; 80(5):2884-92. PubMed ID: 25658978.
    Abstract:
    An efficient one-pot synthesis of highly functionalized multisubstituted benzo[b]thiophenes and their hetero-fused analogues, such as thieno[2,3-b]thiophenes, indolo[2,3-b]thiophenes, and pyrazolo[3,2-c]thiophenes, has been reported. The overall strategy involves sequential base-mediated condensation of 2-bromohet(aryl)acetonitrile precursors with (het)aryl/alkyl dithioesters or other thiocarbonyl species such as dimethyl trithiocarbonate, S-methyl xanthates, methyl N-imidazolyl dithioate, N-alkyl dithiocarbamate, and phenyl isothiocyanate, followed by intramolecular copper-catalyzed arylthiolation of in situ generated enethiolates, furnishing a broad range of 2-functionalized 3-cyanobenzo[b]- and/hetero-fused thiophenes in high yields.
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