Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2015 Jan 21;137(2):624-7.
doi: 10.1021/ja511913h. Epub 2015 Jan 12.

Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides

Affiliations

Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides

Adam Noble et al. J Am Chem Soc. .

Abstract

Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild, operationally simple reaction conditions.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1. Mechanism of Decarboxylative Olefination

References

    1. van Santen R. A. In Catalysis: From Principles to Applications, 1st ed.; Beller M., Renken A., van Santen R. A., Eds.; Wiley-VCH: Weinheim, 2012; p 3.
    1. For selected reviews, see:

    2. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere A., Diederich F., Eds.; Wiley-VCH: Weinheim, 2004.
    3. Seechurn C. C. C. J.; Kitching M. O.; Colacot T. J.; Snieckus V. Angew. Chem., Int. Ed. 2012, 51, 5062. - PubMed
    1. Godula K.; Sames D. Science 2006, 312, 67. - PubMed
    2. Baudoin O. Angew. Chem., Int. Ed. 2007, 46, 1373. - PubMed
    3. Chen X.; Engle K. M.; Wang D.-H.; Yu J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094. - PMC - PubMed
    1. Gooßen L. J.; Deng G.; Levy L. M. Science 2006, 313, 662. - PubMed
    1. For selected reviews, see:

    2. Rodríguez N.; Goossen L. J. Chem. Soc. Rev. 2011, 40, 5030. - PubMed
    3. Gooßen L. J.; Gooßen K. In Topics in Organometallic Chemistry, Vol. 44; Gooßen L. J., Ed.; Springer-Verlag: Berlin, 2013; p 121.
    4. Park K.; Lee S. RSC Adv. 2013, 3, 14165.

Publication types