Topic > Alladium-catalyzed Suzuki cross-coupling reactions and...

Palladium-catalyzed Suzuki cross-coupling reactions and their uses in organic synthesis Palladium-catalyzed cross-coupling reactions are a useful way to create a new carbon bond -carbon with almost quantitative yields and relatively moderate conditions.1,2 This makes them very useful tools in both organic and inorganic synthesis, as well as materials research. The reaction itself was first discovered and studied almost simultaneously in the 1970s by Dr. Akira Suzuki of Hokkaido University, Japan, Dr. Ei-ichi Negishi of Purdue University, and Dr. Richard F. Heck of 'University of Delaware.1 the Nobel Prize in the field of chemistry for their contribution to the development of this method. Certain conditions and reagents are required for the general cross-coupling reaction to occur. A boronic acid such as vinyl, aryl, or alkyl boronic acid used to transfer one of the carbon structures to the palladium complex in the transmetalation step of the reaction. An organic electrophile such as a vinyl halide, aryl halide, or alkyl halide, used to transfer the other carbon structure to the palladium complex in the oxidative addition step of the reaction. A Pd0 catalytic complex protected by a ligand group to protect it from decomposition or oxidation before the reaction begins. These are often produced in situ before the reaction begins as some of them are sensitive to air.1 Examples of Pd0 catalysts used in cross-coupling reactions include palladium dibenzylacetone (Pd2(dba)3), palladium triphenylphosphorus (Pd(PPh3 )4) and palladium chloride (Pd(Cl)2).1,2 Other transition metal catalysts have also been shown to function in cross-coupling reactions with but...... paper medium .... ..actions of organoboron derivatives with organic electrophiles, 1995-1998. J Organomet. Chemistry. 1999, 576, 147-168.4. Total synthesis of a fully protected palytoxin carboxylic acid, Y. Kishi, R.W. Armstrong, J.M. Beau, S.H. Cheon, H. Fujioka, W.H. Ham, L.D. Hawkins, H. Jin, S.H. Kang, M.J. Martinelli, W.W. McWhorter, Jr., M Mizuno, M. Nakata, AE Stutz, FX Talamas, M. Taniguchi, JA Tino, K. Ueda, J.-i. Uenishi, J. B. White, M. Yonaga, J. Am. Chemistry. Soc. 1989, 111, 7525-7530.5. Total synthesis of lucilactaene, an active cell cycle inhibitor in p53-inactive cells. R. S. Coleman, M. C. Walczak, E. L. Campbell, J. Am. Chemistry. Soc. 2005, 127, 16038-16039.6. Soluble poly(para-phenylene). 1. Extension of the Yamamoto synthesis to substituted dibromobenzenes with flexible side chains. M. Rehahn, AD Schluter, G. Wegner, W. Feast, Polymer 1989, 30, 1054-1059.