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. 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.

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Figures

Figure 1
Figure 1
Biaryl-monophosphine Ligands
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