Exploiting the gem-Disubstitution Effect in FcPHOX and HetPHOX P,N Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck Reactions.
The synthesis of a range of novel gem-disubstituted and electronically varied thiophene-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcPHOX) ligands and their application in the Pd-catalyzed intermolecular asymmetric Heck reaction (IAH) is described. These investigations show that gem-disubstitution of i-Pr-PHOX-type ligands can lead to effective and cost-efficient alternatives to the corresponding t-Bu-PHOX systems. The Pd complexes of these ligands were very effective in the IAH, providing phenylated products in up to 100% conversion with up to 97% ee.
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin , Belfield, Dublin 4, Ireland.
Dennis
D
McCartney
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin , Belfield, Dublin 4, Ireland.
Chris
C
Nottingham
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin , Belfield, Dublin 4, Ireland.
Helge
H
Müller-Bunz
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin , Belfield, Dublin 4, Ireland.
Patrick J
PJ
Guiry