Solid-phase organic synthesis Suzuki couplings

A 9-phenylfluoren-9-yl polystyrene-based resin has been described for the attachment of nitrogen and oxygen nucleophiles. Greater acid stability compared to the standard trityl resins that are widely used in solid-phase peptide synthesis make this solid support an interesting alternative in solid-phase organic synthesis. This resin can be used in Suzuki coupling reactions to furnish biaryls in good yields [100]. 

B Chenera, JA Finkelstein, DF Veber. Protodetachable arylsilane polymer linkages for use in solid phase organic synthesis. J Am Chem Soc 117 11999-12000, 1995. Y Han, SD Walker, RN Young. Silicon directed ipso-substitution of polymer bound arylsilanes preparation of biaryls via the Suzuki cross-coupling reaction. Tetrahedron Lett 37 2703-2706, 1996. 

B.iv.b. Suzuki Coupling Reactions. The cross-coupling of organoboron derivatives with carbon electrophiles, the so-called Suzuki reaction (see Sect. IIL2.2 for a review see Ref. [81]), has been conducted in various instances on a solid support. The mild reaction conditions, the compatibility with most functional groups, and the ready availability of starting material (boronic acids) have made this transformation a powerful tool in solid phase organic synthesis. 

Recently, the Suzuki reaction has been extensively developed for solid-phase organic chemistry as a method allowing the parallel synthesis of potential medicinal compounds [108]. Chan et al. reported a versatile polymer-supported 4-[4-methylphenyl(chloro)methyl]-phenoxy linker for the solid-phase synthesis of pseudopeptides based on the Suzuki coupling (Eq. (67)) [109],... 

Due to the substantial amount of literature, even when excluding supported catalysts, only selected articles on the solid phase Suzuki reaction are mentioned here, concentrating on the more recent publications. Apart from the general palladium reviews cited in Sect. 5, some examples of solid phase synthesis can be found in a review of apphcations of the Suzuki-Miyaura cross-coupling reactions in organic synthesis by Kotha in 2002 [114]. 

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