Organic halides coupling reaction with organoboron

S. Suzuki, Cross-Coupling Reactions of Organoboron Compounds with Organic Halides, in Metal-catalyzed Cross-coupling Reactions (F. Diederich, P. J. Stang, Eds.), Wiley-VCH, Weinheim, 1998, 49-89. 

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). 

The cross-coupling reaction of organoboron compounds with organic halides or related electrophiles represents one of the most straightforward methods of carbon-carbon bond... 

Suzuki, A. Cross-coupling reactions of organoboron compounds with organic halides. Metal-Catalyzed Cross-Coupling Reactions 1998,49-97. 

Suzuki, A. Synthetic studies via the cross-coupling reaction of organoboron derivatives with organic halides. Pure Appl. Chem. 1991,63, 419-422. 

Miyaura N (2004) Metal-catalyzed cross-coupling reactions of organoboron compounds with organic halides. In De Meijere A, Diederich F (eds) Metal-catalyzed cross-coupling reactions. Wiley-VCH, Weinheim, p 41... 

Cross-coupling Reactions of Organoboron Compounds with Organic Halides... 

Zapf, A. Coupling of Aryl and Alkyl Halides With Organoboron Reagents (Suzuki Reaction). In Transition Metals for Organic Synthesis (2nd edn), Beller, M. Bolm, C. eds., 2004, 1, 211-229. Wiley-VCH Weinheim, Germany. (Review). 

The traditional synthesis of organoboron compounds from organic halides is based on the reaction of trialkyl borates with Grignard or lithium reagents. However, the cross-coupling reaction of diboron solves the difficulties associated with the use of Mg/Li compounds. The cross-coupling reaction of diborons... 

---