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Preparation of Unsymmetrical Diaryl Selenides via SNAr Reactions in η6-Chloroarene Transition Metal Complexes

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posted on 1999-03-05, 00:00 authored by Andrei A. Vasil'ev, Lars Engman, J. Peter Storm, Carl-Magnus Andersson
Unsymmetrical diaryl selenides were prepared by nucleophilic displacement of chloride with areneselenolates in η6-(arene) Cr(CO)3, FeCpPF6, and Mn(CO)3PF6 complexes. Areneselenolates were conveniently generated in situ by hydrazine reduction of the corresponding diaryl diselenides and reacted with chloroarene Cr(CO)3 complexes in dimethyl sulfoxide at 70 °C. The reactivity of the cationic FeCpPF6 and Mn(CO)3PF6 chloroarene complexes was substantially higher, affording substitution products at ambient temperature in ethanol with areneselenolates generated by sodium borohydride reduction. Intermediate (arylseleno)arene chromium and iron complexes were isolated and characterized by 77Se NMR. As compared with the free diaryl selenide, complexation caused a 20−45 ppm downfield shift.

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    Organometallics

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    chloroarenesodium borohydride reductiondiaryl selenideUnsymmetrical Diaryl Selenides77 Se NMRsubstitution productsambient temperaturenucleophilic displacementcationic FeCpPF 6S N Ar Reactionsη 6Mndimethyl sulfoxideChloroarene Transition Metal Complexes Unsymmetrical diaryl selenidesareneselenolateiron complexesdiaryl diselenideshydrazine reductionCrFeCpPF 6

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