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

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,...

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Bibliographic Details
Published inHeterocycles Vol. 80; no. 2; pp. 1215 - 1226
Main Authors Naber, John R., Fors, Brett P., Wu, Xiaoxing, Gunn, Jonathon T., Buchwald, Stephen L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.03.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
Aryl Mesylate
Palladium Catalysis
OXIDATIVE ADDITION
SUZUKI-MIYAURA
IODIDES
Aryl Tosylate
AMINATION
C-C Bond Formation
Stille Reaction
CHLORIDES
ACTIVE CATALYST
INHIBITORS
FLUORENE
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Summary: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.
Bibliography:NIH RePORTER
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-09-S(S)105