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Issue 33, 2015
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Utility of a heterogeneous palladium catalyst for the synthesis of a molecular semiconductor via Stille, Suzuki, and direct heteroarylation cross-coupling reactions

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Abstract

The commercially available silica-supported heterogeneous catalyst SiliaCat® DPP-Pd has proven to be highly active, robust, and reusable for the synthesis of a thiophene–phthalimide-based molecular semiconductor under microwave-irradiation reaction conditions. A Stille reaction protocol demonstrated that SiliaCat® DPP-Pd outperformed well-known homogeneous catalysts, Pd(PPh3)4 and Pd(PPh3)2Cl2, in terms of performance and catalyst loading, while also exhibiting tolerance to ambient reaction conditions and two-fold recyclability for the formation of product. The success established for SiliaCat® DPP-Pd catalyzed Stille reactions via microwave irradiation was extended to optimize Suzuki coupling and direct heteroarylation protocols. Notably, direct heteroarylation with SiliaCat® DPP-Pd exhibited excellent selectivity and perturbed the formation of homo-coupled aryl bromides, two side reactions that are known to plague this type of cross-coupling reaction.

Graphical abstract: Utility of a heterogeneous palladium catalyst for the synthesis of a molecular semiconductor via Stille, Suzuki, and direct heteroarylation cross-coupling reactions

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Supplementary files

Article information


Submitted
08 Feb 2015
Accepted
27 Feb 2015
First published
27 Feb 2015

This article is Open Access

RSC Adv., 2015,5, 26097-26106
Article type
Paper
Author version available

Utility of a heterogeneous palladium catalyst for the synthesis of a molecular semiconductor via Stille, Suzuki, and direct heteroarylation cross-coupling reactions

S. M. McAfee, J. S. J. McCahill, C. M. Macaulay, A. D. Hendsbee and G. C. Welch, RSC Adv., 2015, 5, 26097
DOI: 10.1039/C5RA02468D

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