Synlett 2016; 27(18): 2567-2570
DOI: 10.1055/s-0035-1562736
letter
© Georg Thieme Verlag Stuttgart · New York

Zirconium-Catalyzed Reactions of 1-Alkynyl Phosphine Oxides and Sulfides with Et3Al

Ilfir R. Ramazanov*
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   eMail: ilfir.ramazanov@gmail.com
,
Rita N. Kadikova
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   eMail: ilfir.ramazanov@gmail.com
,
Zukhra R. Saitova
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   eMail: ilfir.ramazanov@gmail.com
,
Zifa I. Nadrshina
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   eMail: ilfir.ramazanov@gmail.com
,
Usein M. Dzhemilev
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   eMail: ilfir.ramazanov@gmail.com
› Institutsangaben
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Publikationsverlauf

Received: 31. März 2016

Accepted after revision: 22. Juli 2016

Publikationsdatum:
04. August 2016 (online)


Abstract

The interaction of 1-alkynyl phosphine oxides, sulfides, and selenides with Me3Al and Et3Al under zirconocene catalysis was studied. It has been found that the pathway of the reaction of 1-alkynyl phosphine derivatives with Et3Al strongly depends on the nature of the substrate and the solvent. The ethylalumination takes place in the case of 1-alkynyl phosphine oxides in hexane solvent. The reaction of 1-hexynyl phosphine oxide with Et3Al failed when dichloromethane was used as a solvent. Zirconium-catalyzed reaction of 1-heptynyl phosphine sulfide with Et3Al proceeds as the cycloalumination followed by the desulfurization under the action of low-valent zirconium complexes. 1-Heptynyl phosphine selenide was subjected to full deselenation under the reaction conditions.

Supporting Information

 
  • References and Notes

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