Pd‐PEPPSI‐IHeptCl: A General‐Purpose,Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs
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| Authors: | Dr. Bruce Atwater Dr. Nalin Chandrasoma Dr. David Mitchell Dr. Michael J. Rodriguez Prof. Michael G. Organ |
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| Affiliation: | 1. Department of Chemistry, York University, Toronto M3J1P3, Ontario, Canada;2. Lilly Research Laboratories, Indianapolis, IN, USA;3. Centre for Catalysis Research and Innovation (CCRI) and Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada |
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| Abstract: | Dichloro[1,3‐bis(2,6‐di‐4‐heptylphenyl)imidazol‐2‐ylidene](3‐chloropyridyl)palladium(II) (Pd‐PEPPSI‐IHeptCl), 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. |
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| Keywords: | cross-coupling palladium PEPPSI secondary alkylzinc synthetic methods |
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