Palladium catalyzed cross-coupling reactions are a useful way to create a new carbon-carbon bond in near 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 researched almost simultaneously in the 1970’s 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.
In order for the general cross-coupling reaction to take place certain conditions and reagents are needed. A boronic acid such as vinylic, aryl, or alkyl boronic acid that is 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 vinylic halide, aryl halide, or alkyl halide, that is used to transfer the other carbon structure to the palladium complex in the oxidative addition step of the reaction. A Pd0 catalyst complex that is protected by a ligand group in order to protect it from decomposition or oxidation before the reaction begins. These are often made in situ before the reaction begins due to some of them being air sensitive.1 Examples of the Pd0 catalysts that are 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 proven to work in cross-coupling reactions as well with ma...
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...ctions of organoboron derivatives with organic electrophiles, 1995-1998. J Organomet. Chem. 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, A. E. Stutz, F. X. Talamas, M. Taniguchi, J. A. Tino, K. Ueda, J.-i. Uenishi, J. B. White, M. Yonaga, J. Am. Chem. Soc. 1989, 111, 7525-7530.
5. Total Synthesis of Lucilactaene, A Cell Cycle Inhibitor Active in p53-Inactive Cells. R. S. Coleman, M. C. Walczak, E. L. Campbell, J. Am. Chem. Soc. 2005, 127, 16038-16039.
6. Soluble poly(para-phenylene)s. 1. Extension of the Yamamoto synthesis to dibromobenzenes substituted with flexible side chains. M. Rehahn, A.D. Schluter, G. Wegner, W. Feast, Polymer 1989, 30, 1054-1059.
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