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...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-08, Vol.72 (17), p.6464-6472
Main Authors: Hansen, Anders L, Ebran, Jean-Philippe, Gøgsig, Thomas M, Skrydstrup, Troels
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Chemistry
Exact sciences and technology
Gas Chromatography-Mass Spectrometry
Magnetic Resonance Spectroscopy
Organic chemistry
Phosphates - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070912k