The Suzuki-Miyaura cross-coupling reaction

These procedures require activation (heating and sonication, respectively), and yields are only moderate to good. Better results are obtained using 

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Chamoin S, Houldsworth S, Kruse CG, Bakker WI, Snieckus V. The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes. Tetrahedron Lett 1998 39 4179-4182. 

Kotha S, Lahiri S, Kashinath D (2002) Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis. Tetrahedron 58 9633-9695... 

Chamoin, S. Houldsworth, S. Kruse, C. G. Bakker, W. I. Snieckus, V. The Suzuki-Miyaura Cross Coupling Reactions on Solid Support. Link to Solution Phase Directed ortho Metalation. The Leznoff Acetal Linker Approach to Biaryl and Heterobiaryl Aldehydes, Tetrahedron Lett. 1998, 39, 4179-4182. 

Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides Application of the Suzuki—Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids... 

Havelkova, M. Hocek, M. Cesnek, M. Dvorak, D. The Suzuki-Miyaura Cross-Coupling Reactions of 6-Halopurines with Bo-ronic Acids Leading to 6-Aryl- and 6-Alkenylpurines. Synlett 1999, 1145-1147. 

S. Kotha, K. Lahiri, D. Kashinath, Recent Applications of the Suzuki-Miyaura Cross-Coupling Reaction in Organic Synthesis, Tetrahedron 2002, 58, 9633-9695. 

The Suzuki-Miyaura Cross-Coupling Reactions of 2-, 6- or 8-Halopurines with Boronic Acids Leading to 2-, 6- or 8-Aryl- and -Alkenylpurine Derivatives... 

Nickel/carbene complexes have also been successfully employed in the Suzuki-Miyaura cross-coupling reaction. One of the first successful applications of this was demonstrated by Blakey and MacMillan, wherein boronic acids were coupled with aryltrimethylammonium salts [52]. It was found that the transformation could be accomplished using 10 mol % Ni(COD)2,... 

Figure 3.63). The palladium(II) complex was used in the Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and benzyl bromide, 2-bromo and 4-bromo benzalde-hyde, respectively [180-182],...

Molander, G. A., Katona, B. W., Machrouhi, F. Development of the Suzuki-Miyaura Cross-Coupling Reaction Use of Air-Stable Potassium Alkynyltrifluoroborates in Aryl Alkynylations. J. Org. Chem. 2002, 67, 8416-8423. 

The Suzuki-Miyaura cross-coupling reaction is a standard method for carbon-carbon bond formation between an aryl halide or triflate and a boronic acid derivative, catalyzed by a palladium-metal complex. As with the Mizoroki-Heck reaction, this cross-coupling reaction has been developed in ionic liquids in order to recycle and reuse the catalyst. In 2000, the first cross-coupling of a halide derivative with phenylboronic acid in [bmim] [BF4] was described. As expected, the reaction proceeded much faster with bromobenzene and iodobenzene, whereas almost no biphenyl 91 was obtained using the chloride derivative (Scheme 36). The ionic liquid allowed the reactivity to be increased, with a turnover number between 72 and 78. Furthermore, the catalyst could be reused repeatedly without loss of activity, even when the reaction was performed under air. Cross-coupling with chlorobenzene was later achieved - although with only a moderate yield (42%) - using ultrasound activation. 

Yamamoto, S.-L Kinoshita, H. Hashimoto, H. Nishina, Y, Facile Preparation of Pd Nanoparticles Supported on Single-Layer Graphene Oxide and Apphcation for the Suzuki-Miyaura Cross-Coupling Reaction. Nanoscale 2014, 6 (12), 6501-6505. 

Since the discovery of the Suzuki-Miyaura cross-coupling reaction in 1979, the effect of various reaction parameters has been thoroughly studied, including bases, hgands, water, and various solvents [1, 2]. This section will outline new developments made over the past decades in further improving the Suzuki-Miyaura cross-coupling conditions. 

Scheme 2.8 Role of copper salts in the Suzuki-Miyaura cross-coupling reaction.

Carboxylates Among various 0-substituted electrophiles, O-acylated phenols share a few distinct advantages over other pseudohahdes (i) they are readily available and affordable, (ii) they are relatively stable substrates to various reaction conditions, and (iii) they can serve as directing groups for aromatic substitution reactions such as directed ortho-metallations (DoMs) [58]. Moreover, these carboxylates are much more environmentally friendly, generating acetate salts as the only by-product in the Suzuki-Miyaura cross-coupling reaction [59,... 

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