Suzuki cross coupling Further developments

Recently, Caddick and Cloke have developed an extension of this procedure that allows the use of alkyl bromides as coupling partners. The basic changes consist of a stoichiometric amount of the bulkier KO Bu instead of KOMe to activate the borane, and the addition of AgOTf to the reaction mixture [119]. These results, although poor in terms of yield, clearly confirm that sp -sp Suzuki-Miyaura cross-couplings are possible and should be further developed (Scheme 6.35). 

The discovery, use, and further development of cross-coupling reactions have mightily advanced the field of organic synthesis. Today, chemists routinely use Stille, Suzuki, Sonogashira, and Negishi reactions to construct new C-C bonds, and this step is often the key to successful synthesis of incredibly complex... 

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. 

First, Suzuki and coworkers reported Cul-mediated synthesis of diaryl tellurides via C—Te cross-coupling of aryl iodides with benzene teUurolate ions [194]. Catalytic protocol has been subsequently developed using Cul/l,10-phenanthroline L80 for the coupling of aryl iodides with organotellurolates [195] (Scheme 20.58). Further improvement was achieved in the coupling of ditellurides with boronic acid derivatives using copper-based catalytic systems, Cul-bpy [166], CuCl-bpy [196], and CuSO -5H2O/l,10-phenanthroline [197]. 

---