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Issue 45, 2019
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Oxovanadium(v)-catalyzed deoxygenative homocoupling reaction of alcohols

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Abstract

Oxovanadium(V)-catalyzed transformation of alcohols in the presence of hydrazine derivatives was demonstrated. The direct hydrazination reaction of 1,3-diphenylprop-2-en-1-ol with 1,1-diphenylhydrazine in the presence of VO(OSiPh3)3 as a catalyst and MS3A as a dehydrating reagent proceeded to afford the corresponding hydrazination product. On the contrary, the utilization of 1,1-dimethylhydrazine instead of 1,1-diphenylhydrazine was found to induce the deoxygenative homocoupling reaction of the allyl alcohol to give the corresponding 1,5-diene as a major product. In addition to the deoxygenative homocoupling product, the allyl amine into which aniline was introduced was also obtained by using 1,2-diphenylhydrazine in the reaction of 1,3-diphenyl-2-methylprop-2-en-1-ol. Oxovanadium(V)-catalyzed deoxygenative homocoupling reaction of benzyl alcohols could also be performed in the presence of 1,1-dimethylhydrazine.

Graphical abstract: Oxovanadium(v)-catalyzed deoxygenative homocoupling reaction of alcohols

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Publication details

The article was received on 13 Apr 2019, accepted on 12 Jul 2019 and first published on 12 Jul 2019


Article type: Paper
DOI: 10.1039/C9NJ01905G
New J. Chem., 2019,43, 17571-17576

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    Oxovanadium(V)-catalyzed deoxygenative homocoupling reaction of alcohols

    T. Sakuramoto, Y. Donaka, M. Tobisu and T. Moriuchi, New J. Chem., 2019, 43, 17571
    DOI: 10.1039/C9NJ01905G

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