Suzuki cross coupling Synthesis applications

To demonstrate the applicability of this support in organic synthesis, the authors immobilized a (p-bromophenyl) acetic acid which was then transformed into the corresponding biaryl by means of the Suzuki cross-coupling reaction with p-methylphenylboronic acid. Quantitative NaOH cleavage of the ester linkage yielded the released biaryl, of which no purity was mentioned. 

We recently reported the synthesis of a perfluoroalkylsulfonyl linker attached to TentaGel resin 13 (Fig. 6), which proves to act in a fashion similar to triflates as we had hoped, and demonstrated its application for the traceless cleavage of phenols using palladium-catalyzed reduction and Suzuki cross-coupling reactions.3,4... 

In the following the development is presented of a general approach for the synthesis of symmetrically and differently l,4" -substituted p-quaterphenylenes by application of a reliable Suzuki cross-coupling strategy. Experimental details are not given here but can be found elsewhere [51-53]. Note that organic synthesis is a key step for the bottom-up nanotechnology approach. 

Panek and co-workers reported their synthesis of discodermolide in 2005 [62, 63], relying on the application of their crotylsilane methodology for the synthesis of polypropionate motifs [155,156] (see [157] forareview) [158,159,182], Their strategy involved key bond disconnections at C6-C7 and C14-05, based on an aldol coupling and the established Suzuki cross-coupling respectively, employing the key subunits 137 (C1-C6), 138 (C7-C14) and 81 (C15-C24) (Scheme 29). 

The Af-isopropyl-Af-trimethylsilylcarbamoyl-DMG may be conveniently installed via treatment of a phenol with isopropyl isocyanate followed by a one-flask operation that begins the reaction with TMS triflate, lithiation with BuLi/TMEDA, and concludes with electrophile quench (eq 53). The application of this methodology was demonstrated for the synthesis of hydroxy-biaryls. The regiospecific construction of a diverse set of isomeric chlorodihydroxybiphenyls and polychlorinated diphenyls is reported by applying BuLi-mediated DoM protocols and Suzuki cross-coupling tactics on commercially available starting materials. ... 

The Suzuki coupling can be applied on simple and more complex substrates. Industrial applications can be found in the synthesis of the drug losartan or the fungizide boscalid. " Gaukroger et al. synthesized both Z and E isomers of anticancer drug (Z)-combretastatin A-4 via a Suzuki cross-coupling reaction of an arylboronic acid and either (Z)- or ( )-vinyl bromide (Scheme 5-59). ... 

Intermolecular Suzuki Cross-coupling Reactions of Functionalized Alkenylborane Derivates Application in Natural Product Synthesis (Alkenyl B-Alkenyl Coupling)... 

Scheme 3.86 Application of B-alkyl Suzuki cross-coupling for the synthesis of natural and unnatural amino acids.

Piechaczyk O, Doux M, Ricard L, Le Floch P (2005) Synthesis of 1-phosphabarrelene phosphine sulfide substituted palladium(ll) complexes application in the catalyzed suzuki cross-coupling process and in the allylation of secondary amines. Organometallics 24 1204—1213... 

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

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... 

S. R. Chemler, D. Trauner, S. J. Danishefsky, The R-Alkyl Suzuki-Miayura Cross-Coupling Reaction Development, Mechanistic Study, and Applications in Natural Product Synthesis, Angew. Chem. Int. Ed. Engl. 2001, 40, 4544-4568. 

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

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