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J Am Chem Soc. 2008 Aug 20;130(33):10848-9. doi: 10.1021/ja802533u. Epub 2008 Jul 29.

Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates.

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1
Center for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5. sgorelsk@uottawa.ca

Abstract

The concerted metalation-deprotonation mechanism predicts relative reactivity and regioselectivity for a diverse set of arenes spanning the entire spectrum of known palladium-catalyzed direct arylation coupling partners. An analysis following an active strain model provides a more complete portrayal of the important arene/catalyst parameters leading to a successful coupling. The breadth of arenes whose reactivity can be predicted by the CMD mechanism indicates that it may be far more widespread than previously imagined.

PMID:
18661978
DOI:
10.1021/ja802533u
[Indexed for MEDLINE]
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