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Issue 26, 2018
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Palladium catalyzed chloroethoxylation of aromatic and heteroaromatic chlorides: an orthogonal functionalization of a chloroethoxy linker

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Abstract

A novel disconnection based on cross-coupling chemistry was designed to access pharmaceutically relevant aryl-aminoethyl ethers. The developed palladium-catalyzed functionalization of aryl- and heteroaryl chlorides with a sodium tetrakis-(2-chloroethoxy) borate salt is orthogonal to the simple nucleophilic replacement of the chloro function of the ethylene linker. The transformation enables efficient 2-chloroethoxylation in the absence of an additional external base. Subsequent amine substitution of the alkyl halide affords 2-aminoethoxy arenes. The applicability of this method was demonstrated through the synthesis of various aryl- and heteroaryl-alkyl ethers, including the intermediates of marketed drug molecules.

Graphical abstract: Palladium catalyzed chloroethoxylation of aromatic and heteroaromatic chlorides: an orthogonal functionalization of a chloroethoxy linker

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Publication details

The article was received on 18 May 2018, accepted on 15 Jun 2018 and first published on 15 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01146J
Citation: Org. Biomol. Chem., 2018,16, 4895-4899
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    Palladium catalyzed chloroethoxylation of aromatic and heteroaromatic chlorides: an orthogonal functionalization of a chloroethoxy linker

    B. Pethő, D. Vangel, J. T. Csenki, M. Zwillinger and Z. Novák, Org. Biomol. Chem., 2018, 16, 4895
    DOI: 10.1039/C8OB01146J

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