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Synfacts 2018; 14(03): 0315
DOI: 10.1055/s-0037-1609276
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Magnetic Pd- and CuO-Catalyzed Regioselective Direct Arylation of Anilides

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Vásquez-Céspedes S. Holtkamp M. Karst U. Glorius F. * Westfälische Wilhelms-Universität Münster, Germany
Reusable and Magnetic Palladium and Copper Oxide Catalysts in Direct ortho and meta Arylation of Anilide Derivatives.

Synlett 2017;
28: 2759-2764
Article in Thieme ConnectGoogle Scholar
Further Information

Publication History

Publication Date:
15 February 2018 (online)

 
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Key words

palladium catalysis - copper catalysis - magnetite - arylation - anilides

Significance

Magnetite-supported copper oxide (CuO/Fe3O4) or palladium nanoparticles (Pd/Fe3O4) catalyzed the regioselective direct arylation of anilides with diaryliodonium triflates in 1,2-dichloroethane. CuO/Fe3O4 exclusively afforded the meta arylation products in up to 99% yield, whereas Pd/Fe3O4 gave ortho arylation products in up to 89% yield.


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Comment

In the direct arylation of N-(o-tolyl)pivalamide with diphenyliodonium triflate, CuO/Fe3O4 was magnetically recovered and reused four times without loss of its catalytic performance. On the other hand, the catalytic activity of Pd/Fe3O4decreased after one recycling. Hot filtration tests and TXRF analysis indicated that catalytically active soluble species were generated in situ from CuO/Fe3O4 and Pd/Fe3O4 during the reaction.


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