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HERO ID
5310670
Reference Type
Journal Article
Title
STILLE CROSS-COUPLING REACTIONS OF ARYL MESYLATES AND TOSYLATES USING A BIARYLPHOSPHINE BASED CATALYST SYSTEM
Author(s)
Naber, JR; Fors, BP; Wu, X; Gunn, JT; Buchwald, SL
Year
2010
Is Peer Reviewed?
Yes
Journal
Heterocycles
ISSN:
0385-5414
Volume
80
Issue
2
Page Numbers
1215-1226
Language
English
PMID
23596345
DOI
10.3987/COM-09-S(S)105
Web of Science Id
WOS:000276939500045
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.
Keywords
Aryl Mesylate; Palladium Catalysis; C-C Bond Formation; Stille Reaction; Aryl Tosylate
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