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
. 2010 Feb 26;80(2):1215-1226.
doi: 10.3987/COM-09-S(S)105.

STILLE CROSS-COUPLING REACTIONS OF ARYL MESYLATES AND TOSYLATES USING A BIARYLPHOSPHINE BASED CATALYST SYSTEM

John R Naber  1 , Brett P Fors, Xiaoxing Wu, Jonathon Gunn, Stephen L Buchwald
Affiliations

STILLE CROSS-COUPLING REACTIONS OF ARYL MESYLATES AND TOSYLATES USING A BIARYLPHOSPHINE BASED CATALYST SYSTEM

John R Naber et al. Heterocycles. .

Abstract

A catalyst system for the Stille cross-coupling reactions of aryl mesylates and tosylates is reported. Using the combination of Pd(OAc)2, XPhos, and CsF in t-BuOH an array of aryl and heteroaryl sulfonates were successfully employed in these reactions. Morever, heteroarylstannanes, such as furyl, thiophenyl, and N-methylpyrrole, which are often prone to decomposition, were efficiently coupled under these conditions. Ortho-substitution on the stannane coupling partner was well tolerated; however, the presence of ortho substituents on the aryl sulfonates greatly reduced the proficiency of these reactions.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Biaryl-monophosphine Ligands
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. For reviews of the Stille reaction see: Mitchell TN. In: ‘Metal-catalyzed Cross-coupling Reactions. 2. de Meijere A, Diederich F, editors. Wiley-VCH; Weinheim: 2004. p. 125.Espinet P, Echavarren AM. Angew Chem Int Ed. 2004;43:4704.

    1. Kosugi M, Sasazawa K, Shimizu Y, Migita T. Chem Lett. 1977:301.
    1. Milstein D, Stille JK. J Am Chem Soc. 1978;100:3636.
    2. Milstein D, Stille JK. J Org Chem. 1979;44:1613.
    3. Stille JK. Pure Appl Chem. 1985;57:1771.
    1. Lord AM, Mahon MF, Lloyd MD, Threadgill MD. J Med Chem. 2009;52:868. - PubMed
    2. Amans D, Bellosta V, Cossy J. Org Lett. 2007;9:4761. - PubMed
    3. Cullen MD, Deng BL, Hartman TL, Watson KM, Buckheit RW, Pannecouque C, DeClercq E, Cushman M. J Med Chem. 2007;50:4854. - PubMed
    4. Uchil V, Seo B, Nair V. J Org Chem. 2007;72:8577. - PMC - PubMed
    1. Sofiyev V, Navarro G, Trauner D. Org Lett. 2008;10:149. - PubMed
    2. Lopez S, Montenegro J, Saa C. J Org Chem. 2007;72:9572. - PubMed
    3. Schweitzer D, Kane JJ, Strand D, McHenry P, Tenniswood M, Helquist P. Org Lett. 2007;9:4619. - PubMed

LinkOut - more resources