Issue 43, 2021

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

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.

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

Associated articles

Supplementary files

Article information

Article type
Edge Article
Submitted
01 sep 2021
Accepted
15 okt 2021
First published
15 okt 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

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

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.

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