C-H Arylation of Unsubstituted Furan and Thiophene with Acceptor' Bromides: 
Access to Donor-Acceptor-Donor-Type Building Blocks for Organic Electronics

Matsidik, Rukiya; Martin, Johannes; Schmidt, Simon; Obermayer, Johannes; Lombeck, Florian; Nuebling, Fritz; Komber, Hartrnut; Fazzi, Daniele; Sommer, Michael

doi:10.1021/jo502432e

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C-H Arylation of Unsubstituted Furan and Thiophene with Acceptor' Bromides: Access to Donor-Acceptor-Donor-Type Building Blocks for Organic Electronics

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Fazzi, Daniele
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Matsidik, R., Martin, J., Schmidt, S., Obermayer, J., Lombeck, F., Nuebling, F., et al. (2015). C-H Arylation of Unsubstituted Furan and Thiophene with Acceptor' Bromides: Access to Donor-Acceptor-Donor-Type Building Blocks for Organic Electronics. Journal of Organic Chemistry, 80(2), 980-987. doi:10.1021/jo502432e.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0028-18FC-C

Abstract

Pd-catalyzed direct arylation (DA) reaction conditions have been established for unsubstituted furan (Fu) and thiophene (Th) with three popular acceptor building blocks to be used in materials for organic electronics, namely 4,7-dibromo-2,1,3-benzothiadiazole (BTBr₂), N,N'-dialkylated 2,6-dibromonaphthalene-1,4,5,8-bis(dicarboximide) (NDIBr₂), and 1,4-dibromotetrafluorobenzene (F₄Br₂). Reactions with BTBr₂, F₂Br₄, and NDIBr₂ require different solvents to obtain high yields. The use of dimethylacetamide (DMAc) is essential for the successful coupling of BTBr₂ and F₄Br₂, but detrimental for NDIBr₂, as the electron-deficient NDI core is prone to nucleophilic core substitution in DMAc as solvent but not in toluene. NDIFu₂ is much more planar compared to NDITh₄, resulting in an enhanced charge-transfer character, which makes it an interesting building block for conjugated systems designed for organic electronics. This study highlights direct arylation as a simple and inexpensive method to construct a series of important donor-acceptor-donor building blocks to be further used for the preparation of a variety of conjugated materials.