Cross-coupling organoboron with organic electrophiles

The cross-coupling reaction of organoboron compounds with organic halides or triflates proceeds selectively in the presence of a base, such as sodium or potassium carbonate, phosphate, hydroxide, and alkoxide [11, 45], The bases can be used in aqueous solution, or in suspension in dioxane or DMF. In contrast, the cross-coupling reaction with certain electrophiles, such as allylic acetates [45], 1,3-butadiene monoxide [49], and propargyl carbonates [50], occurs under neutral conditions without any assistance from a base. The transmetallation of organoboron compounds with palladium halides under basic or neutral conditions can be considered to involve three routes, 1, 2, and 3 (Schemes 2-18, 2-20, and 2-23, below). 

Suzuki, A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles. J. Organomet. 

A. R. Martin, Y. Yang, Palladium Catalyzed Cross-Coupling Reactions of Organoboronic Acids with Organic Electrophiles "Acta Chem. Scand. 1993, 47, 221-230. 

Martin, A. R., Yang, Y. Paiiadium-catalyzed cross-coupling reactions of organoboronic acids with organic electrophiles. Acta Chem. Scand. 1993,47, 221-230. 

State-of-the-Art in Metal-Catalyzed Cross-Coupling Reactions of Organoboron Compounds with Organic Electrophiles... 

The cross-coupling of organoboron reagents with organic electrophiles in the presence of a base and a Pd catalyst is commonly referred to as the Suzuki-Miyaura reaction and has proved to be one of the most popular cross-coupling methodologies... 

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