Scope of direct arylation of fluorinated aromatics with aryl sulfonates

Organic & Biomolecular Chemistry
Joyce Wei Wei ChangJayasree Seayad

Abstract

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.

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Citations

Mar 5, 2016·Journal of the American Chemical Society·Marco SimonettiIgor Larrosa
Jun 16, 2017·The Journal of Organic Chemistry·Zubaoyi YiDipannita Kalyani
Aug 25, 2017·Organic & Biomolecular Chemistry·Anoir HfaiedhHenri Doucet
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Apr 13, 2019·Chemistry : a European Journal·Shuxin MaoHenri Doucet
Feb 16, 2021·Organic & Biomolecular Chemistry·Rebecca J EllabyJennifer R Hiscock
Apr 3, 2021·Catalysis Science & Technology·Tongliang Zhou, Michal Szostak
Apr 29, 2021·Organic & Biomolecular Chemistry·Timofey D MoseevOleg N Chupakhin
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Mar 15, 2018·The Journal of Organic Chemistry·Xinzhe ShiHenri Doucet
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Dec 26, 2018·The Journal of Organic Chemistry·Roman Yu PeshkovEvgeny V Tretyakov

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