Facile and scalable synthesis of the fused-ring heterocycles thieno[3,2-b]thiophene and thieno[3,2-b]furan

John T Henssler; Adam J Matzger

doi:10.1021/ol9010745

Facile and scalable synthesis of the fused-ring heterocycles thieno[3,2-b]thiophene and thieno[3,2-b]furan

Org Lett. 2009 Jul 16;11(14):3144-7. doi: 10.1021/ol9010745.

Authors

John T Henssler¹, Adam J Matzger

Affiliation

¹ Department of Chemistry and the Macromolecular Science and Engineering Program, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.

PMID: 19548691
DOI: 10.1021/ol9010745

Abstract

An optimized synthetic methodology which allows for efficient and scalable access to the important fused-ring heterocycle thieno[3,2-b]thiophene and the first reported isolation of thieno[3,2-b]furan is presented. The properties of thieno[3,2-b]furan were assessed through a detailed analysis of the NMR data and an investigation of the chemical reactivity. Thieno[3,2-b]furan is chemically robust and offers good selectivity toward functionalization at the 2-position via bromination and the 5-position via deprotonation.