Scope of direct arylation of fluorinated aromatics with aryl sulfonates

The scope and limitations of direct arylation of fluorinated aromatics with aryl sulfonates was examined. Pd(OAc)(2), in the presence of MePhos and KOAc in THF, efficiently catalyzed the direct arylation of fluoro aromatics with aryl triflates under ambient conditions. Sterically hindered triflates...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-03, Vol.10 (11), p.2289-2299
Hauptverfasser: Chang, Joyce Wei Wei, Chia, Eugene Yurong, Chai, Christina Li Lin, Seayad, Jayasree
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Sprache:eng
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Zusammenfassung:The scope and limitations of direct arylation of fluorinated aromatics with aryl sulfonates was examined. Pd(OAc)(2), in the presence of MePhos and KOAc in THF, efficiently catalyzed the direct arylation of fluoro aromatics with aryl triflates under ambient conditions. Sterically hindered triflates and heteroaryl triflates gave good to excellent yields of the cross coupled products using a modified catalyst system which involves Pd(OAc)(2)-RuPhos at 100 °C. The direct arylation of electron deficient arenes with aryl mesylates is also established using Pd(OAc)(2)-SPhos as the catalyst in toluene-(t)BuOH at 120 °C.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob06840k