학술논문
Beyond Directed orthoMetalation:Ruthenium-Catalyzed Amide-Directed CAr–OMe Activation/Cross-CouplingReaction of Naphthamides with Aryl Boronates.
Document Type
Article
Author
Source
Subject
*METALATION
*RUTHENIUM catalysts
*AMIDES
*ACTIVATION (Chemistry)
*AMIDE synthesis
*COUPLING reactions (Chemistry)
*AROMATIC compounds
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Language
ISSN
1523-7060
Abstract
A new and generalsynthetic methodology for the construction ofbiaryl, heterobiaryl, and polyaryl molecules by the ruthenium-catalyzedcross-coupling of ortho-methoxy naphthamides witharyl boroneopentylates is described. The isomeric 1-MeO-2-naphthamidesand 2-MeO-1-naphthamides furnish an expansive series of arylated naphthamidesin excellent yields. Competition experiments showed the higher reactivityof 1-MeO-2-naphthamide over 2-MeO-benzamide. Orthogonality betweenthe C–O activation/cross-coupling and the Suzuki–Miyaurareactions was established. The method provides naphthalenes whichare difficult to prepare by directed orthometalation. [ABSTRACT FROM AUTHOR]