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Pd‐PEPPSI‐IHept Cl : A General‐Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs
Author(s) -
Atwater Bruce,
Chandrasoma Nalin,
Mitchell David,
Rodriguez Michael J.,
Organ Michael G.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603603
Subject(s) - carbene , reductive elimination , catalysis , alkyl , chemistry , migratory insertion , oxidative addition , palladium , selectivity , medicinal chemistry , coupling (piping) , photochemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
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.