Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 16, 2020
Previous Article Next Article

Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]thiophenes and benzo[4,5]selenopheno[3,2-b]thiophenes using the Fiesselmann thiophene synthesis

Author affiliations

Abstract

A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann thiophene synthesis. To realize this strategy, the Friedel–Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]thiophene and benzo[4,5]selenopheno[3,2-b]thiophene are of interest for further elaboration of organic semiconductor materials.

Graphical abstract: Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]thiophenes and benzo[4,5]selenopheno[3,2-b]thiophenes using the Fiesselmann thiophene synthesis

Back to tab navigation

Supplementary files

Article information


Submitted
10 Feb 2020
Accepted
02 Apr 2020
First published
02 Apr 2020

Org. Biomol. Chem., 2020,18, 3164-3168
Article type
Paper

Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]thiophenes and benzo[4,5]selenopheno[3,2-b]thiophenes using the Fiesselmann thiophene synthesis

R. A. Irgashev, N. S. Demina and G. L. Rusinov, Org. Biomol. Chem., 2020, 18, 3164
DOI: 10.1039/D0OB00300J

Social activity

Search articles by author

Spotlight

Advertisements