title: Investigations on the Suzuki-Miyaura and Negishi couplings with alkenyl phosphates: application to the synthesis of 1,1-disubstituted alkenes.
abstract: The development of versatile Suzuki-Miyaura and Negishi cross-couplings with nonactivated alkenyl phosphates and aromatic boronic acids or organozinc reagents was achieved in acceptable to good yields. A series of 1,1-disubstituted alkenes were synthesized using a combination of either Ni(COD)2/Cy3P/K3PO4 or Pd2dba3/DPPF in THF. When working with alkenyl electrophiles in metal-catalyzed cross-couplings, this method lends itself as a less costly and more stable alternative to the corresponding triflate or nonaflate derivatives. In addition, initial studies are presented regarding an efficient 1,2-migration under Negishi coupling conditions.
authors.affiliation: The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
authors.forename: Anders L
authors.initials: AL
authors.lastname: Hansen
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Ebran
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Gøgsig
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010710:Phosphates / Q000737:chemistry*
chemical_list: D000475:Alkenes; D010710:Phosphates