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PEPPSI
PEPPSI is an abbreviation for pyridine-enhanced precatalyst preparation stabilization and initiation. It refers to a group of palladium catalysts developed around 2005 by Prof. Michael G. Organ and co-workers at York University,〔Organ, M. G. Rational catalyst design and its application in sp3-sp3 couplings. Presented at the 230th National Meeting of the American Chemical Society, Washington, DC, 2005; Abstract 308.〕 which can accelerate various aminations and cross-coupling reactions. In comparison to many alternative palladium catalysts, PEPPSI-type complexes are stable to air and moisture and are relatively easy to synthesize and handle. ==Structure and synthesis== In the basic structure of PEPPSI, R can be a methyl (CH3, Me), ethyl (C2H5, Et), isopropyl (C3H7, ''i''Pr), isopentyl (C5H11, ''i''Pent), or isoheptyl (C7H15, ''i''Hept) group, and the resulting catalysts are thus labeled as PEPPSI-IMes, PEPPSI-IEt, PEPPSI-IPr, PEPPSI-IPent, and PEPPSI-IHept respectively, with or without "Pd-" added in front. Contrary to common palladium-based catalysts, such as tetrakis(triphenylphosphine)palladium(0), PEPPSI is stable to exposure to air〔Jie Jack Li, E. J. Corey (Name reactions for homologations, Part 1 ), John Wiley and Sons, 2009, ISBN 0-470-08507-X p. 74〕 and moisture. Even heating in dimethyl sulfoxide at 120 °C for hours does not result in significant decomposition or neutralization of PEPPSI catalysts.〔 The synthesis and structure of PEPPSI catalysts were presented in 2005〔〔 and published in 2006.〔(Issue cover of Chemistry – A European Journal, June 2006 )〕 PEPPSI catalysts are based on an organometallic complex palladium ''N''-heterocyclic carbene (NHC). They can be obtained by reacting imidazolium salt, palladium(II) chloride, and potassium carbonate in a 3-chloropyridine solvent, under vigorous stirring at 80 °C for 16 hours in air. The yield of PEPPSI in this reaction is 97–98%.〔(PEPPSI Catalysts ), Sigma Aldrich〕〔
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