When SF5 outplays CF3: effects of pentafluorosulfanyl decorated scorpionates on copper

Anurag Noonikara-Poyil; Alvaro Muñoz-Castro; Andrii Boretskyi; Pavel K. Mykhailiuk; H. V. Rasika Dias

doi:10.1039/D1SC04846E

When SF₅ outplays CF₃: effects of pentafluorosulfanyl decorated scorpionates on copper†

Anurag Noonikara-Poyil,

^a Alvaro Muñoz-Castro,^b Andrii Boretskyi,^c Pavel K. Mykhailiuk

*^de and H. V. Rasika Dias

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, TX 76019, USA
E-mail: dias@uta.edu

^b Grupo de Química Inorgánica y Materiales Moleculares, Facultad de Ingeniería, Universidad Autonoma de Chile, El Llano Subercaseaux 2801, Santiago, Chile

^c UORSY, Ukrorgsyntez Ltd, 02002 Kyiv, Ukraine

^d Enamine Ltd, Chervonotkatska 78, Kyiv, Ukraine

^e Chemistry Department, Taras Shevchenko National University of Kyiv, Volodymyrska 64, 01601 Kyiv, Ukraine
E-mail: Pavel.Mykhailiuk@gmail.com

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.

This article is part of the themed collection: Most popular 2021 main group, inorganic and organometallic chemistry articles, 2021

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DOI: https://doi.org/10.1039/D1SC04846E
Article type: Edge Article
Submitted: 01 Sep 2021
Accepted: 15 Oct 2021
First published: 15 Oct 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2021,12, 14618-14623

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When SF₅ outplays CF₃: effects of pentafluorosulfanyl decorated scorpionates on copper

A. Noonikara-Poyil, A. Muñoz-Castro, A. Boretskyi, P. K. Mykhailiuk and H. V. R. Dias, Chem. Sci., 2021, 12, 14618 DOI: 10.1039/D1SC04846E

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