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Facile γ ‐C−H Bond Activation in Phosphinoamine Ligands Resulting in Regio‐ and Stereoselective C−C Coupling with Terminal Acetylenes
Author(s) -
Slugovc Christian,
Mauthner Klaus,
Kacetl Martin,
Mereiter Kurt,
Schmid Roland,
Kirchner Karl
Publication year - 1998
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/(sici)1521-3765(19981002)4:10<2043::aid-chem2043>3.0.co;2-5
Subject(s) - stereoselectivity , terminal (telecommunication) , coupling (piping) , chemistry , stereochemistry , double bond , catalysis , polymer chemistry , materials science , organic chemistry , computer science , telecommunications , metallurgy
Novel C−C coupling products are afforded from the reaction of tris(pyrazolyl)borate ruthenium complexes, containing the phosphinoamine ligands Ph 2 PCH 2 CH 2 NMe 2 , Ph 2 PCH 2 CH 2 NEt 2 , and Ph 2 PCH 2 CH 2 N i Pr 2 , with terminal acetylenes (see scheme). The coupling takes place regioselectively at the γ ‐carbon atom of the phosphinoamine ligand and, depending on the steric requirments of R, either at the internal or terminal carbon atom of the acetylene molecule. All these reactions proceed in a highly diastereoselective fashion.