We report the oxidative dimerization reaction that creates a new γ-γ C-C bond by using a catalytic amount of the iron(II) salt and benzoyl peroxide as the terminal oxidant. The concept is hypothesized to rely on dienol ethers serving as the radical precursor which leads to the generation of a radical cation that undergoes a highly selective γ-homocoupling reaction. The transformation demonstrates a broad substrate scope, encompassing cyclic and acyclic dienol silyl ethers. Mechanistic studies are currently under investigation including kinetics, Hammett plot, Eyring analysis, EPR, radical clock, and radical trapping. This gamma-gamma dimerization was a key step in the total synthesis of the Honokiol analog.

Iron-mediated gamma-gamma dimerization

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ACS Fall 2022

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