Mixed iodonium-, phosphonium-, arsonium-, sulfoniumdiazonium ylides in reactions with nucleophiles

Abstract

The reactions of mixed ylides containing a diazonium fragment and an "onium" group of different nature with nucleophiles were studied. In the iodonium-diazonium and sulfoniumdiazonium ylide, the nucleophile first of all substitutes the iodonium and sulfonium group. A series of hetaryl-substituted phosphazines was obtained by a one-pot process of nucleophilic substitution in a diazonium-iodonium ylide with subsequent nucleophilic addition of triarylphosphine at the diazo group.

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Correspondence to T. A. Podrugina.

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Dedicated to the memory of Academician of the Russian Academy of Sciences Nikolai Serafimovich Zefirov (1935–2017), a then team leader who inspired this work.

Organisch-Chemisches Institut der Universität Heidelberg im Neuenheimer Feld, 270 D-69120 Heidelberg, Germany.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0284–0292, February, 2019.

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Podrugina, T.A., Pavlova, A.S., Vinogradov, D.S. et al. Mixed iodonium-, phosphonium-, arsonium-, sulfoniumdiazonium ylides in reactions with nucleophiles. Russ Chem Bull 68, 284–292 (2019). https://doi.org/10.1007/s11172-019-2384-8

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Key words

  • mixed ylides
  • iodonium-diazonium ylides
  • arsonium-diazonium ylides
  • sulfonium-diazonium ylides
  • nucleophilic substitution
  • nucleophilic addition
  • phosphazines
  • triarylphosphines