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Nucleophilic Trapping of π‐Allylpalladium Intermediates Generated by Carbopalladation of Bicyclopropylidene: A Novel Three‐Component Reaction
Author(s) -
Nüske Hanno,
Noltemeyer Mathias,
de Meijere Armin
Publication year - 2001
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 - 10.1002/1521-3773(20010917)40:18<3411::aid-anie3411>3.0.co;2-d
Subject(s) - chemistry , nucleophile , iodide , tris , medicinal chemistry , trapping , stereochemistry , catalysis , organic chemistry , ecology , biology , biochemistry
The primary carbopalladation intermediate resulting under Heck conditions from bicyclopropylidene and phenyl iodide in the presence of tris( α ‐furyl)phosphane rearranges to give a π‐allylpalladium complex which is efficiently trapped by various nucleophiles R n XH. This rearrangement leads to substituted methylenecyclopropanes in good to excellent yields (42–99 %) [Eq. (1); X=C ( n =3), N ( n =2), O ( n =1)]. The intermediate 1,1‐dimethyleneallylpalladium complex was isolated and fully characterized by an X‐ray crystal‐structure analysis.