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C(sp 3 )–N Bond‐Forming Reductive Elimination of Amines: Reactions of Bisphosphine‐Ligated Benzylpalladium(II) Diarylamido Complexes
Author(s) -
Marquard Seth L.,
Rosenfeld Devon C.,
Hartwig John F.
Publication year - 2010
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.200904032
Subject(s) - reductive elimination , chemistry , dissociation (chemistry) , nucleophile , ferrocene , ligand (biochemistry) , medicinal chemistry , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , electrochemistry , receptor , biochemistry , electrode
A rare event : The benzylpalladium amido complex 1 (Ar=napthyl) was used to study the mechanism of an unusual reductive elimination of amines (see scheme). The observed inversion of configuration is proposed to result from dissociation of the amido ligand, followed by nucleophilic attack on the benzylic carbon atom. binap=2,2′‐bis(diphenylphosphanyl)‐1,1′‐binaphthyl, dppf=1,1′‐bis(diphenylphosphanyl)ferrocene.