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Synthesis 2021; 53(14): 2422-2434
DOI: 10.1055/a-1416-4924
DOI: 10.1055/a-1416-4924
paper
A Simple and Efficient Synthesis of Fused Benzo[b]thiophene Derivatives
This work was supported by the Russian Science Foundation (Grant No. 20-73-10043).
Abstract
A new approach to the synthesis of fused benzothiophene derivatives was developed based on iodine-promoted photocyclization of 4,5-diaryl-substituted thiophenes obtained in three steps from commercially available compounds. Comparative analysis showed that photochemical cyclization is a more efficient method for the preparation of fused benzo[b]thiophene derivatives, compared to oxidative coupling of 4,5-diaryl-substituted thiophenes in the presence of iron(III) chloride and palladium-catalyzed intramolecular arylation. This new approach provides an efficient synthesis of functionally substituted naphtho[2,1-b:3,4-b′]dithiophenes, phenanthro[9,10-b]thiophenes, benzo[1,2-b:3,4-b′:6,5-b′′]trithiophenes, as well as new fused heterocycles containing a pyridine ring and/or a carbazole moiety.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1416-4924.
- Supporting Information
Publication History
Received: 28 January 2021
Accepted after revision: 08 March 2021
Accepted Manuscript online:
08 March 2021
Article published online:
12 April 2021
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