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Volume 80, Issue 2 ( March, 1, 2010 ), Pages 1215-1226
Received, 4th August, 2009, Accepted, 25th August, 2009, Published online, 27th August, 2009.
DOI: 10.3987/COM-09-S(S)105 |
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| Stille Cross-Coupling Reactions of Aryl Mesylates and Tosylates Using a Biarylphosphine Based Catalyst System |
John R. Naber, Brett P. Fors, Xiaoxing Wu, Jonathon T. Gunn, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, U.S.A. |
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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, thienyl, and N-methylpyrrolyl, 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 efficiency of these reactions. |
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Graphical Abstract
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Keywords
1. Aryl Mesylate
2. Palladium Catalysis
3. C-C Bond Formation
4. Stille Reaction
5. Aryl Tosylate
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| Corresponding author; email: sbuchwal@mit.edu |
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