Organoboron compounds, Suzuki reaction

Palladium-catalyzed carbon-carbon bond forming reactions like the Suzuki reac-tion as well as the Heck reaction and the Stille reaction, have in recent years gained increased importance in synthetic organic chemistry. In case of the Suzuki reaction, an organoboron compound—usually a boronic acid—is reacted with an aryl (or alkenyl, or alkynyl) halide in the presence of a palladium catalyst. 

Cross-coupling with organoboron compounds (the Suzuki-Miyaura reaction) is by far the most popular and versatile method of cross-coupling, and has been extensively reviewed.3-5... 

Organoboron compounds cannot react without proper activation. The use of oxygen bases is inherent in the standard Suzuki-Miyaura cross-coupling method. Fluorides (usually CsF) can be used as alternative activating agents, which is particularly useful in cases when the reagents are incompatible with oxygen bases for the reactions run under anhydrous conditions,24 (66) 241 Fluoride activation can be effective, however, even under aqueous phase-transfer conditions (67) 242... 

Miyaura, N. Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds, Chem. Rev. 1995, 95, 2457-2483. 

Palladium catalysts have been found which are effective in the Suzuki coupling reaction of arylboronic acids with aryl chlorides carrying electron-withdrawing groups.73 Biaryls may also be synthesized by cross-coupling of arylboronic acids with arenediazonium salts.74,75 There has been a report of the polymer-bound palladium-catalysed Suzuki coupling of aryl triflates with organoboron compounds.76 Arylbor-onates may themselves be synthesized by the palladium-catalysed reactions of... 

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. 

MiyauraN, Suzuki A (1995) Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95 2457-2483... 

The use of solid supported, recyclable catalysts, is a well-assessed technique in classic organic chemistry, and many exhaustive reviews dealing with this subject are available [105, 115]. The use of solid supported catalysts for library synthesis in solution has also been reported. Among others, Kobayashi et al. presented the use of a new supported scandium catalyst for 3CC reactions leading to solution libraries of amino ketones, esters, and nitriles (24-member model discrete library) [116], or to quinolines (15-member model discrete library) [117], and Jang [118] presented a polymer bound Pd-catalyzed Suzuki coupling of organoboron compounds with halides and triflates. This area was also briefly reviewed recently [119]. 

Oh-e, T., Miyaura, N., and Suzuki, A. (1993). Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates. J Org Chem 58 2201-2208. 

The Suzuki Reaction Coupling Reactions with Organoboron Compounds ... 

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