When SF5 outplays CF3: effects of pentafluorosulfanyl decorated scorpionates on copper |
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| Authors: | Anurag Noonikara-Poyil Alvaro Muoz-Castro Andrii Boretskyi Pavel K Mykhailiuk H V Rasika Dias |
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| Institution: | Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington TX 76019 USA.; Grupo de Química Inorgánica y Materiales Moleculares, Facultad de Ingeniería, Universidad Autonoma de Chile, El Llano Subercaseaux 2801, Santiago Chile ; UORSY, Ukrorgsyntez Ltd, PO Box 59 02002 Kyiv Ukraine ; Enamine Ltd, Chervonotkatska 78, 02094 Kyiv Ukraine ; Chemistry Department, Taras Shevchenko National University of Kyiv, Volodymyrska 64, 01601 Kyiv Ukraine, |
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| Abstract: | Polyfluorinated, electron-withdrawing, and sterically demanding supporting ligands are of significant value in chemistry. Here we report the assembly and use of a bis(pyrazolyl)borate, Ph2B(3-(SF5)Pz)2]− that combines all such features, and involves underutilized pentafluorosulfanyl substituents. The ethylene and carbonyl chemistry of copper(i) supported by Ph2B(3-(SF5)Pz)2]−, a comparison to the trifluoromethylated counterparts involving Ph2B(3-(CF3)Pz)2]−, as well as copper catalyzed cyclopropanation of styrene with ethyl diazoacetate and CF3CHN2 are presented. The results from cyclopropanation show that SF5 groups dramatically improved the yields and stereoselectivity compared to the CF3.Copper–ethylene and carbonyl complexes of the newly developed Ph2B(3-(SF5)Pz)2]− enable the study of ligand steric and electronic effects caused by the –SF5 group (dubbed “super CF3”), and a comparison to the –CF3 bearing analogs. |
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