<p>The deoxygenation of alcohols is an important research area in modern organic chemistry that has been studied extensively. However, a chemoselective and clean method is still desirable for the emerging large scale bio-chemicals production. Herein, we report a method for alcohols deoxygenation to alkanesusing hydrogen as the reductant assisted by iodide without metal catalyst. This method is simple and green without consume quantitative extra reagents. Substrate scope study showed that this method tolerated a broad scope of functional groups including phenyl, naphthyl and allyl alcohol derivatives. Kinetics study revealed that the C-I (formed by hydroxyl group substituted by iodide) cleavage was the rate-determining step. Mechanistic study suggested a radical mechanism for this alcohol deoxygenation reactions.</p> Graphical Abstract <p></p>

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Metal-Free Iodide-Assisted Reductive Deoxygenation of Alcohols Using Molecular Hydrogen

  • Haikuan Yang,
  • Jihong Zhang,
  • Xiang Ye,
  • Fengying Qiu,
  • Haiwei Jiang,
  • Mingfeng Dong,
  • Yang Peng

摘要

The deoxygenation of alcohols is an important research area in modern organic chemistry that has been studied extensively. However, a chemoselective and clean method is still desirable for the emerging large scale bio-chemicals production. Herein, we report a method for alcohols deoxygenation to alkanesusing hydrogen as the reductant assisted by iodide without metal catalyst. This method is simple and green without consume quantitative extra reagents. Substrate scope study showed that this method tolerated a broad scope of functional groups including phenyl, naphthyl and allyl alcohol derivatives. Kinetics study revealed that the C-I (formed by hydroxyl group substituted by iodide) cleavage was the rate-determining step. Mechanistic study suggested a radical mechanism for this alcohol deoxygenation reactions.

Graphical Abstract