Synthesis 2019; 51(04): 859-864
DOI: 10.1055/s-0037-1611017
paper
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of Benzo[1,2-b:6,5-b′:3,4-c′′]trithiophenes Starting from Thiophene

Hyokwon Kim
,
Kyukwan Zong*
Institute of Fusion Science, Division of Science Education, Department of Chemistry Education, Chonbuk National University, Jeonju, Jeonbuk, 561-756, Republic of Korea   Email: kzong@jbnu.ac.kr
› Author Affiliations
This work was partially supported by NRF-2017R1D1A1B03031393. The authors declare no competing financial interest.
Further Information

Publication History

Received: 21 August 2018

Accepted after revision: 17 September 2018

Publication Date:
10 October 2018 (eFirst)

Abstract

A series of benzo[1,2-b:6,5-b′:3,4-c′′]trithiophenes were synthesized in four steps starting from thiophene. Thiophene was converted into 2,5-dialkylthiophenes upon dilithiation followed by treatment with various alkyl halides. The reaction of 2,5-dialkylthiophenes with Br2 easily afforded the corresponding 2,5-dialkyl-3,4-dibromothiophenes. Their coupling reactions with 3-tributyltinthiophene in the presence of a Pd catalyst and the subsequent oxidative ring-closing reactions led to target compounds in moderate to good yields.

 
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