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

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...

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Bibliographic Details
Published in:ACS catalysis 2011-03, Vol.1 (3), p.170-174
Main Authors: Hickman, Amanda J, Sanford, Melanie S
Format: Article
Language:eng ; jpn
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/cs1001543