Issue 45, 2019

Oxovanadium(v)-catalyzed deoxygenative homocoupling reaction of alcohols

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

Supplementary files

Article information

Article type
Paper
Submitted
13 abr 2019
Accepted
12 jul 2019
First published
12 jul 2019

New J. Chem., 2019,43, 17571-17576

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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