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

Supplementary files

Article information

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

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

Download Citation

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

Permissions

Request permissions

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Science