Palladium(II)-catalyzed coupling reactions with a chelating vinyl ether and arylboronic acids: a new Heck/Suzuki domino diarylation reaction

Alejandro Trejos; Ashkan Fardost; Samir Yahiaoui; Mats Larhed

doi:10.1039/B918358B

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Chemical Communications

Issue 48, 2009

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Palladium(II)-catalyzed coupling reactions with a chelating vinyl ether and arylboronic acids: a new Heck/Suzuki domino diarylation reaction

Alejandro Trejos , Ashkan Fardost , Samir Yahiaoui and Mats Larhed

Chem. Commun., 2009, 7587-7589

DOI: 10.1039/B918358B
Received 07 Sep 2009, Accepted 20 Oct 2009
First published on the web 05 Nov 2009

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Abstract
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A mild and novel palladium(II)-catalyzed domino Heck/Suzuki α,β-diarylation-reduction of a dimethylaminoethyl substituted chelating vinyl ether was developed by using electron-rich arylboronic acids in combination with p-benzoquinone. Based on the preparative results, a catalytic cycle is proposed. Further, highly regioselective palladium(II)-catalyzed α- or β-monoarylation of the chelating vinyl ether was achieved using either a bidentate ligand or by employing ligand-less conditions.

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Supplementary Info

Experimental details, UV/ELSD, ESI-MS, ¹H and ¹³C NMR spectra of products
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Chemical Communications

Palladium(II)-catalyzed coupling reactions with a chelating vinyl ether and arylboronic acids: a new Heck/Suzuki domino diarylation reaction

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