title: Pd-PEPPSI-IHept(Cl) : A General-Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs.
abstract: Dichloro[1,3-bis(2,6-di-4-heptylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) (Pd-PEPPSI-IHept(Cl) ), a new, very bulky yet flexible Pd-N-heterocyclic carbene (NHC) complex has been evaluated in the cross-coupling of secondary alkylzinc reactants with a wide variety of oxidative addition partners in high yields and excellent selectivity. The desired, direct reductive elimination branched products were obtained with no sign of migratory insertion across electron-rich and electron-poor aromatics and all forms of heteroaromatics (five and six membered). Impressively, there is no impact of substituents at the site of reductive elimination (i.e., ortho or even di-ortho), which has not yet been demonstrated by another catalyst system to date.
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto M3J1P3, Ontario, Canada.
authors.forename: Bruce
authors.initials: B
authors.lastname: Atwater
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto M3J1P3, Ontario, Canada.
authors.forename: Nalin
authors.initials: N
authors.lastname: Chandrasoma
authors.affiliation: Lilly Research Laboratories, Indianapolis, IN, 46285, USA.
authors.forename: David
authors.initials: D
authors.lastname: Mitchell
authors.affiliation: Lilly Research Laboratories, Indianapolis, IN, 46285, USA.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Rodriguez
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto M3J1P3, Ontario, Canada. organ@uottawa.ca.|Centre for Catalysis Research and Innovation (CCRI) and Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada. organ@uottawa.ca.
authors.forename: Michael G
authors.identifier: http://orcid.org/0000-0002-4625-5696
authors.initials: MG
authors.lastname: Organ
keywords: PEPPSI; cross-coupling; palladium; secondary alkylzinc; synthetic methods