Suzuki-Miyaura coupling chemistry

This chemistry features in a synthesis of the left hand fragment of yessotoxin and adriatoxin <02OL3943>. Assembly of the F-N ring component of gymnomycin A, involves a b-alkyl Suzuki-Miyaura coupling reaction <02OL1747>. 

Polymer-stabilized palladium nanoparticles (or nanoclusters) [125-127] have recently received increasing attention in the field of synthetic organic chemistry [128, 129]. Thus, for example, the poly(iV-vinyl-2-pyrrolidone) (PVP)-supported Pd particle catalyzed the Suzuki-Miyaura coupling in water [130]. Poly(amidoamine) (PAMAM) dendrimer-encapsulated palladium nanoparticles were designed and prepared to provide highly selective catalysts for hydrogenation of olefins [131-133]. Hyperbranched aromatic amides (aramids) and PS-DVB-methacryloylethylenesulfonic acid resin have also been... 

The Suzuki-Miyaura coupling has found widespread applications in materials chemistry, below are a few recent examples that harness the coupling protocol to produce novel materials. 

Chapter 10—Organohalides. A discussion of synthesizing alkyl fluorides from alcohols has been added to Section 10.5 to reflect the increasing importance of fluorinated compounds in pharmaceutical chemistry. Coverage of the palladium-catalyzed Suzuki-Miyaura coupling reaction has been added to Section 10.7. 

The time consuming chromatographical purification of heterocycles 28 and 29 slowed down the rate of library production. A phase separation using fluorous chemistry was employed by Zhang and Lu to address the workup and purification of fused 3-aminoimidazo[ l,2-a]pyridines (such as 30) [54]. Thus, attachment of a perfluorooctanesulfonyl tag to aldehydes and subsequent Ugi three-component microwave-assisted condensations with 2-aminopyridines and isocyanides furnished the desired heterocycles 30, which were conveniently isolated by fluorous solid-phase extraction. The fluorous tag could be subsequently used as an activating group in the post-condensation modifications, such as Suzuki-Miyaura cross-coupling reactions. 

In the last quarter-century, the practice and art of organic synthesis has been revolutionized by the discovery of transition metal catalyzed organic transformations, at a rate that would make the discoverer of islands in the St. Lawrence Seaway envious [78]. Aside from the demonstrated DoM-Ar-Ar cross-coupling connection above and the initial promise of acy-lative, 200 — 201 (Scheme 49) [79] and carbonylative, 202 —> 203 —> 204 or Suzuki-Miyaura, 203 — 205 (Scheme 50) [80] coupling, the establishment of potential DoM links to the literature-visible, already reliable, but not yet mature Heck, Sonogashira, and Grubbs metatheses will undoubtedly reap benefits for synthetic aromatic and heteroaromatic chemistry. 

Alkylboronic acids and arylboronic acids, RB(OH)2, and ArB(OH)2, respectively, are increasingly important in organic chemistry. The palladium catalyzed coupling reaction of aryl halides and aryl triflates with arylboronic acids (the Suzuki-Miyaura... 

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