Cross-coupling reactions catalyzed by palladium and their uses in organic synthesis Cross-coupling reactions catalyzed by palladium are a useful way to create a new bond carbon-carbon with almost quantitative yields and relatively moderate conditions.1,2 This makes them very useful tools in 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 the University of Delaware.1 They received the Nobel Prize in the field of chemistry for their contributions to the development of this method. For the general cross-coupling reaction to take place, certain conditions and reagents are necessary. A boronic acid such as vinyl, aryl, or alkylboronic acid that is used to transfer one of the carbon structures to the palladium complex during the transmetallation step of the reaction. An organic electrophile such as a vinyl halide, aryl halide, or alkyl halide, which is used to transfer the other carbon structure to the palladium complex during the oxidative addition step of the reaction. A Pd0 catalyst complex that is protected by a ligand group to protect it from decomposition or oxidation before the reaction begins. These are often made in situ before the reaction begins because some of them are air sensitive.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 coupling reactions as well. crossed with middle of paper.... ..actions of organoboron derivatives with organic electrophiles, 1995-1998. J Organomet. Chemical. 1999, 576, 147-168.4. Total Synthesis of a Fully Protected Palytoxin Carboxylic Acid, Y. Kishi, RW Armstrong, JM Beau, SH Cheon, H. Fujioka, WH Ham, LD Hawkins, H. Jin, SH Kang, MJ Martinelli, WW McWhorter, Jr. , M Mizuno, M. Nakata, AE Stutz, FX Talamas, M. Taniguchi, JA Tino, K. Ueda, J.-i. Uenishi, JB White, M. Yonaga, J. Am. Chemical. Soc. 1989, 111, 7525-7530.5. Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells. RS Coleman, MC Walczak, EL Campbell, J. Am. Chemical. Soc. 2005, 127, 16038-16039.6. Soluble poly(para-phenylene). 1. Extension of the Yamamoto synthesis to dibromobenzenes substituted with flexible side chains. M. Rehahn, AD Schluter, G. Wegner, W. Feast, Polymer 1989, 30, 1054-1059.