PEPPSI

PEPPSI is an abbreviation for pyridine-enhanced precatalyst preparation stabilization and initiation. It refers to a family of commercially available^[1]^[2]^[3] palladium catalysts developed around 2005 by Prof. Michael G. Organ and co-workers at York University,^[4]^[5] which can accelerate various carbon-carbon and carbon-heteroatom^[6] bond forming cross-coupling reactions. In comparison to many alternative palladium catalysts, Pd-PEPPSI-type complexes are stable to air and moisture and are relatively easy to synthesize and handle.

^ Cite error: The named reference sigma-PEPPSI was invoked but never defined (see the help page).
^ PEPPSI™-IPent for Demanding Cross-Coupling Reactions, Sigma-Aldrich
^ PEPPSI Catalyst, Sigma-Aldrich ChemFiles
^ Hadei, N.; Kantchev, E.A.B.; O'Brien, C.J.; Chass, G.; Hunter, H.H.; Penner, G.; Hopkinson, A.C.; Organ, M.G. (2005). Rational catalyst design and its application in sp³-sp³ couplings. 230th ACS National Meeting. Washington, DC: American Chemical Society. pp. Abstract 308.
^ Hadei, N.; Kantchev, E.A.B.; O'Brien, C.J.; Organ, M.G. (2005). "The First Negishi Cross-Coupling Reaction of Two Alkyl Centers Utilizing a Pd−N-Heterocyclic Carbene (NHC) Catalyst". Org. Lett. 7: 3805–3807. doi:10.1021/ol0514909. PMID 16092880.
^ Valente, C.; Pompeo, M.; Sayah, M.; Organ, M.G. (2014). "Carbon–Heteroatom Coupling Using Pd-PEPPSI Complexes". Organic Process Research & Development. 18: 180–190. doi:10.1021/op400278d.

[sigma-PEPPSI-1] Cite error: The named reference sigma-PEPPSI was invoked but never defined (see the help page).

[sigma-PEPPSI-IPent-2] PEPPSI™-IPent for Demanding Cross-Coupling Reactions, Sigma-Aldrich

[Aldrich-ChemFiles-3] PEPPSI Catalyst, Sigma-Aldrich ChemFiles

[Organ-ACS-2005-4] Hadei, N.; Kantchev, E.A.B.; O'Brien, C.J.; Chass, G.; Hunter, H.H.; Penner, G.; Hopkinson, A.C.; Organ, M.G. (2005). Rational catalyst design and its application in sp³-sp³ couplings. 230th ACS National Meeting. Washington, DC: American Chemical Society. pp. Abstract 308.

[Hadei-2005-5] Hadei, N.; Kantchev, E.A.B.; O'Brien, C.J.; Organ, M.G. (2005). "The First Negishi Cross-Coupling Reaction of Two Alkyl Centers Utilizing a Pd−N-Heterocyclic Carbene (NHC) Catalyst". Org. Lett. 7: 3805–3807. doi:10.1021/ol0514909. PMID 16092880.

[OPRD-2014-6] Valente, C.; Pompeo, M.; Sayah, M.; Organ, M.G. (2014). "Carbon–Heteroatom Coupling Using Pd-PEPPSI Complexes". Organic Process Research & Development. 18: 180–190. doi:10.1021/op400278d.

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