학술논문

Beyond Directed ortho Metalation: Ru-Catalyzed CAr--O Activation/Cross-Coupling Reaction by Amide Chelation.
Document Type
Article
Source
Journal of the American Chemical Society. 8/13/2014, Vol. 136 Issue 32, p11224-11227. 4p.
Subject
*METALATION
*RUTHENIUM catalysts
*COUPLING reactions (Chemistry)
*CHELATION
*AMIDES
*BENZAMIDE
Language
ISSN
0002-7863
Abstract
Disclosed is a new, catalytic, and general methodology for the chemical synthesis of biaryl, heterobiaryl, and polyaryl molecules by the cross-coupling of o-methoxybenzamides with aryl boroneopentylates. The reaction is based on the activation of the unreactive C-OMe bond by the proximate amide directing group using catalytic RuH2(CO)(PPh3)3 conditions. A one-step, base-free coupling process is thereby established that has the potential to supersede the useful two-step directed ortho metalation/cross-coupling reaction involving cryogenic temperature and strong base conditions. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, minimum waste, and convenient scale-up make these reactions suitable for industrial applications. [ABSTRACT FROM AUTHOR]