Abstract
CC bond formation directly from biomass-derived oxidized hydrocarbons with carbonucleophile utilizing hydrogen auto-transfer is intriguing because it does not generate waste. We demonstrate the use of oxidized terpenes derived from natural sources such as essential oils for the direct alkylation of oxindoles employing a well-defined earth-abundant low-valent iron complex. The scope of the reaction is extremely broad, and numerous terpenols, including geraniol, nerol, prenol, farnesol, geranylgeraniol, phytol, and solanesol, can be utilized. Furthermore, the developed method can also extend to non-natural synthetic terpenols. A plausible catalytic cycle is proposed based on a series of in-depth mechanistic studies, kinetic experiments, and DFT analyses.
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