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.
Exploiting the gem-Disubstitution Effect in FcPHOX and HetPHOX P,N Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck Reactions. -The asymmetric Pd-catalyzed arylation of dihydrofurans is achieved under microwave irradiation and in the presence of chiral oxazoline ligands. -(MCCARTNEY, D.; NOTTINGHAM, C.; MUELLER-BUNZ, H.; GUIRY*, P. J.; J. Org. Chem. 80 (2015) 20, 10151-10162, http://dx.doi.org/10.1021/acs.joc.5b01764 ; Cent. Synth. Chem. Biol., Univ. Coll., Dublin 4, Ire.; Eng.) -F. Berndt
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