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Catalyst Control of Site Selectivity in the PdII/IV-Catalyzed Direct Arylation of Naphthalene

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Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States
Cite this: ACS Catal. 2011, 1, 3, 170–174
Publication Date (Web):January 25, 2011
Copyright © 2011 American Chemical Society

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    This letter describes a new method for the highly site- and chemoselective Pd-catalyzed direct arylation of naphthalene. Tuning the structure of the diimine-ligated Pd catalyst results in formation of the α-arylated product in high yield and >50:1 selectivity. This is, to our knowledge, the first systematic evaluation of catalyst control in the C−H arylation of an unactivated aromatic substrate. Preliminary studies implicate an unusual mechanism involving sequential naphthalene π-coordination/metalation at PdIV.

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    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect