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A method of mild deoxydichlorination of aldehydes catalyzed by Triphenylphosphine oxide

D. A. Shipilovskikh, M. F. Konkova, I. P. Nikonov, M. M. Gladysheva, S. A. Shipilovskikh

Abstract


The catalytic system of triphenylphosphine oxide and phthaloyl dichloride catalysing conversion of aldehydes to 1,1-dichlorides is reported. The reaction proceeds via a P (V) catalysis manifold in which triphenylphosphine oxide turnover is achieved using phthaloyl dichloride as a consumable reagent. The application of the developed method on substrates of different structures was demonstrated. We showed the use of unsaturated compounds, including aromatics with and without electron donating / withdrawing groups, as well as saturated aliphatic compounds. The possibility of using the developed method on a gram scale was also demonstrated with the deoxydichlorination reaction of 0.03 mol of benzaldehyde catalyzed by triphenylphosphine oxide as an example. The proposed method may be of interest for the production of different herbicides, insecticides and fungicides for the agricultural industry.


Keywords


aldehydes; Lewis base catalysis; organocatalysis; triphenylphosphine oxide; nucleophilic substitution; agricultural chemistry

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References


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DOI: https://doi.org/10.15826/chimtech.2022.9.2.02

Copyright (c) 2022 D.A. Shipilovskikh, M.F. Konkova, I.P. Nikonov, M.M Gladysheva, S.A. Shipilovskikh

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Chimica Techno Acta, 2014-2022
ISSN 2411-1414 (Online)