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 p...

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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
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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:0947-6539
1521-3765
DOI:10.1002/chem.201603603