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
. 2009 Feb;65(9):1785-1789.
doi: 10.1016/j.tet.2008.10.110.

Gold(I)-catalyzed intermolecular hydroarylation of allenes with nucleophilic arenes: scope and limitations

Michael A Tarselli  1 , Ann Liu, Michel R Gagné
Affiliations

Gold(I)-catalyzed intermolecular hydroarylation of allenes with nucleophilic arenes: scope and limitations

Michael A Tarselli et al. Tetrahedron. 2009 Feb.

Abstract

The addition of nucleophilic methoxyarenes to allenes proceeds at room temperature in dichloromethane with a catalytic amount of phosphite-gold(I) precatalyst and silver additive. The addition is regioselective for the allene terminus, and generates E-allylation products without the need for prefunctionalization of the synthons as organometallics or allyl bromides. Coordinating heteroaromatics and sterically hindered allenes do not participate in the reaction.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Arenes tested, which are unreactive under the specified conditions.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Allenes unreactive in the present system.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Anastas P, Warner J. Green Chemistry: Theory and Practice. Oxford University Press; New York, NY: 1998.

    1. For recent (2007–2008) reviews concerning this topic, see: Skouta R, Li C-J. Tetrahedron. 2008;64:4917–4938. Widenhoefer RA. Chem.—Eur. J. 2008;14:5382–5391. Gorin DJ, Toste FD. Nature. 2008;446:395–403. Hashmi ASK. Chem. Rev. 2007;107:3180–3211. Fürstner A, Davies PW. Angew. Chem., Int. Ed. 2007;46:2–42.

    1. Watanabe T, Oishi S, Fujii N, Ohno H. Org. Lett. 2007;9:4821–4824. - PubMed
    1. Zhang Z, Widenhoefer RA. Org. Lett. 2008;10:2079–2081. - PubMed
    1. Nishina N, Yamamoto Y. Angew. Chem., Int. Ed. 2006;45:3314–3317. - PubMed
    2. Nishina N, Yamamoto Y. Synlett. 2007:1767–1770.

LinkOut - more resources