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C(sp 3 )O Bond‐Forming Reductive Elimination of Ethers from Bisphosphine‐Ligated Benzylpalladium(II) Aryloxide Complexes
Author(s) -
Marquard Seth L.,
Hartwig John F.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101088
Subject(s) - reductive elimination , chemistry , dissociation (chemistry) , ligand (biochemistry) , medicinal chemistry , stereochemistry , nucleophile , combinatorial chemistry , ionic bonding , ion , catalysis , organic chemistry , receptor , biochemistry
On the contrary : Isolated benzylpalladium aryloxide complexes undergo C(sp 3 )O bond‐forming reductive elimination by a stepwise ionic mechanism (see scheme) distinct from the accepted concerted pathway for reductive elimination of aromatic ethers from arylpalladium(II) species. The mechanism is proposed to result from dissociation of the aryloxide ligand followed by nucleophilic attack on the benzylic carbon atom.