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Ligand-Controlled Site-Selective Cross-Coupling

  • Miyuki Yamaguchi
  • Kei ManabeEmail author
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 372)

Abstract

Site-selective mono-cross-coupling reactions involving dichloro- or dibromo(hetero)aryl substrates are utilized to prepare substituted monochloro- or monobromo(hetero)arenes, which are used as drug components and synthetic precursors. In these reactions, selectivity toward the preferred reaction site of a dihalo(hetero)arene can vary depending on the ancillary ligand of the transition metal catalyst. This review summarizes the examples of ligand-controlled site-selective cross-coupling reactions, specifically those mediated by Pd complexes.

Keywords

Kumada–Tamao–Corriu coupling Palladium Sonogashira coupling Suzuki–Miyaura coupling Transition metal catalyst 

Abbreviations

Ar

Aryl

Cy

Cyclohexyl

dba

Dibenzylideneacetone

DHTP

Dihydroxyterphenylphosphine

DPEPhos

Bis[2-(diphenylphosphino)phenyl] ether

DPPF

1,1′-Bis(diphenylphosphino)ferrocene

HTP

Hydroxyterphenylphosphine

LUMO

Lowest unoccupied molecular orbital

NMP

N-Methylpyrrolidone

PMP

4-Methoxyphenyl

PXPd2

Dichloro(chlorodi-tert-butylphosphine)palladium(II) dimer

Q-Phos

1,2,3,4,5-Pentaphenyl-1′-(di-tert-butylphosphino)ferrocene

TBAC

Tetrabutylammonium chloride

Th

Thienyl

Tol

4-Methylphenyl

Ts

Tosyl, p-toluenesulfonyl

Xantphos

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

XPhos

2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.School of Pharmaceutical SciencesUniversity of ShizuokaSuruga-kuJapan

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