Efficient synthesis of thieno[3,2-b:4,5-b′]diindoles and benzothieno[3,2-b]indoles by Pd-catalyzed site-selective C–C and C–N coupling reactions?

Organic & Biomolecular Chemistry Pub Date: 2012-09-26 DOI: 10.1039/C2OB26489G

Abstract

Heteroacenes (thieno[3,2-b:4,5-b′]diindoles and benzothieno[3,2-b]indoles) were efficiently synthesized from tetrabromothiophene and 2,3-dibromobenzothiophene in two steps, respectively. In the first step, a site-selective Pd-catalyzed C–C coupling is carried out, followed by a two-fold C–N coupling with aromatic and aliphatic amines.

Graphical abstract: Efficient synthesis of thieno[3,2-b:4,5-b′]diindoles and benzothieno[3,2-b]indoles by Pd-catalyzed site-selective C–C and C–N coupling reactions
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