Pd-PEPPSI-IHept(Cl) : A General-Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs

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...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-10, Vol.22 (41), p.14531-14534
Main Authors: Atwater, Bruce, Chandrasoma, Nalin, Mitchell, David, Rodriguez, Michael J, Organ, Michael G
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:1521-3765
DOI:10.1002/chem.201603603