Synthesis of Thiophene-Based π-Conjugated Oligomers via Ligand-Enabled Pd-Catalyzed Suzuki-Miyaura Coupling of Haloterthienyls

Jie Guo; Yong Wu; Fuk Yee Kwong; Heng Zhang; Aiwen Lei

doi:10.1002/asia.201800395

Synthesis of Thiophene-Based π-Conjugated Oligomers via Ligand-Enabled Pd-Catalyzed Suzuki-Miyaura Coupling of Haloterthienyls

Chem Asian J. 2018 Jul 4;13(13):1660-1663. doi: 10.1002/asia.201800395. Epub 2018 Jun 8.

Authors

Jie Guo¹, Yong Wu^{1

2}, Fuk Yee Kwong², Heng Zhang¹, Aiwen Lei^{1

3}

Affiliations

¹ College of Chemistry and Molecular Sciences, Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072, P. R. China.
² State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. China.
³ National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, Jiangxi, P. R. China.

PMID: 29882391
DOI: 10.1002/asia.201800395

Abstract

A ligand-enabled Pd-catalyzed Suzuki-Miyaura coupling of haloterthienyls for the synthesis of various thiophene-based π-conjugated oligomers including quinquethiophenes is demonstrated. An indolyl phosphine ligand plays an important role in this transformation. Thiopheneboronic acids were well applied, which might open up a window for the application of thiopheneboronic acids in the synthesis of thiophene-based π-conjugated oligomers in materials chemistry.

Keywords: Suzuki-Miyaura coupling; ligand-enabled; quinquethiophene; π-conjugated oligomers.