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Catalysts 2014, 4(3), 307-320; https://doi.org/10.3390/catal4030307

Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes

School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
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Received: 29 May 2014 / Revised: 28 July 2014 / Accepted: 5 August 2014 / Published: 20 August 2014
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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Abstract

Pd-catalyzed, site-selective mono-cross-coupling of substrates with two identical halo groups is a useful method for synthesizing substituted monohalogenated arenes. Such arenes constitute an important class of compounds, which are commonly identified as drug components and synthetic intermediates. Traditionally, these site-selective reactions have been realized in a “substrate-controlled” manner, which is based on the steric and electronic differences between the two carbon-halogen bonds of the substrate. Recently, an alternative strategy, “catalyst-controlled” site-selective cross-coupling, has emerged. In this strategy, the preferred reaction site of a dihaloarene can be switched, merely by changing the catalyst used. This type of selective reaction further expands the utility of Pd-catalyzed cross-coupling. In this review, we summarize the reported examples of catalyst-controlled site-selectivity switching in Pd-catalyzed cross-coupling of dihaloarenes. View Full-Text
Keywords: palladium; Suzuki–Miyaura coupling; site-selectivity; Grignard reagent; phosphine palladium; Suzuki–Miyaura coupling; site-selectivity; Grignard reagent; phosphine
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Manabe, K.; Yamaguchi, M. Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes. Catalysts 2014, 4, 307-320.

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