Insight into the palladium-catalyzed oxidative arylation of benzofuran: heteropoly acid oxidants evoke a Pd(II)/Pd(IV) mechanism

TETRAHEDRON

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Article

Pereira, Kyle C.¹  Porter, Ashley L.¹  Potavathri, Shathaverdhan¹  LeBris, Alexis P.^1,2  DeBoef, Brenton¹ 

[1] Univ Rhode Isl, Dept Chem, Kingston, RI 02881 USA

[2] St Lukes Sch, New Canaan, CT 06840 USA

关键词: C-H functionalization;    Biaryl synthesis;    Heteropoly acid;    Palladium(IV);   

DOI  :  10.1016/j.tet.2013.02.061

来源: Elsevier

【 摘 要 】

The effects of oxidant and organic acid additives on the oxidative cross-coupling reactions of electron rich heterocycles, such as benzofuran with benzene were studied. Both regioselectivity and reaction rate could be controlled by varying the condition parameters. Furthermore, mechanistic insight was achieved via kinetic studies, which indicate that reactions that are oxidized by the heteropoly acid H4PMo11VO40 operate via a Pd(II)/Pd(IV) mechanisms, while reactions oxidized by either AgOAc or Cu(OAc)(2) operate by a Pd(II)/Pd(0) mechanism. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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