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Review
. 2015 Apr 24;20(5):7528-57.
doi: 10.3390/molecules20057528.

Recent developments in the Suzuki-Miyaura reaction: 2010-2014

Irene Maluenda  1 , Oscar Navarro  2
Affiliations
Review

Recent developments in the Suzuki-Miyaura reaction: 2010-2014

Irene Maluenda et al. Molecules. .

Abstract

The Suzuki-Miyaura reaction (SMR), involving the coupling of an organoboron reagent and an organic halide or pseudo-halide in the presence of a palladium or nickel catalyst and a base, has arguably become one of most utilized tools for the construction of a C-C bond. This review intends to be general account of all types of catalytic systems, new coupling partners and applications, including the literature between September 2010 and December 2014.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
SMR with new organoborane coupling partners.
Figure 1
Figure 1
Phosphane-Pd complexes and phosphane ligands used in SMR.
Scheme 2
Scheme 2
Synthesis of axially chiral biaryls.
Figure 2
Figure 2
(NHC)-Pd complexes and NHC ligands used in SMR.
Figure 3
Figure 3
Complexes and ligands used in SMR.
Scheme 3
Scheme 3
SMR of 2-iodoglycals, phenoldiazonium salts and N'-tosylarylhydrazines.
Scheme 4
Scheme 4
Ni-catalyzed SMR using phosphine ligands.
Figure 4
Figure 4
(NHC)nNi(II) complexes used as catalysts in SMR.
Figure 5
Figure 5
Ni(0) complex and ligands used in Ni-catalyzed SMR.
Scheme 5
Scheme 5
Ni-catalyzed asymmetric coupling of unactivated alkyl electrophiles.
Figure 6
Figure 6
Heterogeneous complexes and ligands for SMR.
Figure 7
Figure 7
Ligands and complexes for homogeneous SMR in water.
Figure 8
Figure 8
Heterogeneous catalysts for SMR in water.
Figure 9
Figure 9
SMR in natural product synthesis (I).
Figure 10
Figure 10
SMR in natural product synthesis (II).
Figure 11
Figure 11
SMR in drug synthesis.
Figure 12
Figure 12
SMR in living organisms.
Figure 13
Figure 13
Polymers synthesized using SMP.
See this image and copyright information in PMC

References

    1. Miyaura N., Yamada K., Suzuki A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett. 1979;20:3437–3440. doi: 10.1016/S0040-4039(01)95429-2. - DOI
    1. Miyaura N. Cross-coupling reactions: A practical guide. Top. Curr. Chem. 2002;219:11–59.
    1. Tsuji J. Palladium Reagents and Catalysis. 2nd ed. Wiley; West Sussex, UK: 2004.
    1. De Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. Wiley-VCH; Weinheim, Germany: 2004.
    1. Negishi E. Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley-Interscience; New York, NY, USA: 2002.