Selective Mono and Diborylation of Aromatic Pentafluorosulfanyl Compounds by iridium-catalyzed C–H Activation
Year: 2026
Type: preprint
Abstract: The pentafluorosulfanyl (SF5) group has emerged as a valuable fluorinated motif in medicinal chemistry and materials science, yet methods for the selective diversification of aromatic SF5 compounds remain limited.Herein, we report a systematic study of the iridium-catalyzed C-H borylation strategy that enables the selective mono-and diborylation of aromatic SF5 substrates through appropriate adjustment of the reaction conditions.The methodology displays broad substrate scope, good to excellent regioselectivity and high functional-group tolerance, including free amino, hydroxy and halo substituents.Comparative studies with the corresponding CF3 analogues reveal distinct differences in both reactivity and product distribution, highlighting the specific behaviour of the SF5 substituent under iridiumcatalyzed C-H borylation conditions.The resulting aryl boronate esters serve as versatile intermediates for a broad range of C-C and C-heteroatom bond-forming reactions, providing rapid access to structurally diverse SF₅-containing molecules.This work establishes C-H borylation as a general platform for the diversification of aromatic SF5 compounds and expands the synthetic utility of this emerging class of fluorinated building blocks.
Source: ChemRxiv
Institutions: Lyon 1 Université, Centre National de la Recherche Scientifique, Laboratoire Hydrazines et Composés Energétiques Polyazotés, ArianeGroup (France), University of Bayreuth, Université de Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Institut National des Sciences Appliquées de Lyon
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7211901953