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

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

*  and
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
* Author to whom correspondence should be addressed.
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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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.
Keywords: palladium; Suzuki–Miyaura coupling; site-selectivity; Grignard reagent; phosphine palladium; Suzuki–Miyaura coupling; site-selectivity; Grignard reagent; phosphine
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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