Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 41, Pages 14531-14534Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603603
Keywords
cross-coupling; palladium; PEPPSI; secondary alkylzinc; synthetic methods
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Funding
- NSERC Canada
- Eli Lilly Research Award Program (LRAP)
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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.
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