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

Authors

Kyle C. Pereira, University of Rhode Island
Ashley L. Porter, University of Rhode Island
Shathaverdhan Potavathri, University of Rhode Island
Alexis P. LeBris, University of Rhode Island
Brenton DeBoef, University of Rhode IslandFollow

Document Type

Article

Date of Original Version

2013

Department

Chemistry

Abstract

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.

Citation/Publisher Attribution

Pereira, K. C., Porter, A. L., Potavathri, S., LeBris,A. P., DeBoef, B. (2013). Insight into the palladium-catalyzed oxidative arylation of benzofuran: heteropoly acid oxidants evoke a Pd(II)/Pd(IV) mechanism. Tetrahedron, 69(22), 4429-4435. doi: 10.1016/j.tet.2013.02.061

Available at: http://dx.doi.org/10.1016/j.tet.2013.02.061.