Investigations on the Suzuki-Miyaura and Negishi couplings with alkenyl phosphates: application to the synthesis of 1,1-disubstituted alkenes.
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.
Hansen
Anders L
AL
The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Ebran
Jean-Philippe
JP
Gøgsig
Thomas M
TM
Skrydstrup
Troels
T
D000475:Alkenes / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010710:Phosphates / Q000737:chemistry*
D000475:Alkenes; D010710:Phosphates