Journal
HETEROCYCLES
Volume 80, Issue 2, Pages 1215-1226Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-09-S(S)105
Keywords
Aryl Mesylate; Palladium Catalysis; C-C Bond Formation; Stille Reaction; Aryl Tosylate
Categories
Funding
- National Institutes of Health [GM-46059]
- Merck
- Boehringer Ingelheim
- BASF (Pd(OAc)2)
- Nippon Chemical
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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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