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PreprintCC BY-NC-NDChemRxiv

Selective Mono and Diborylation of Aromatic Pentafluorosulfanyl Compounds by iridium-catalyzed C–H Activation

  • Yibo Qin1
  • Shoubhik Das2
  • Abderrahmane Amgoune3
  • Anis Tlili1
  1. 1Université Lyon 1, CNRS, CNES, ArianeGroup, LHCEP, UMR, Bd du 11, Novembre, France, F-69100
  2. 2Department of Chemistry, University of Bayreuth, Universitätsstraße 30, Bayreuth, Germany, 95447
  3. 3Université de Lyon, CNRS, Université Claude Bernard Lyon 1, ICBMS, INSA Lyon, CPE, UMR5246
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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.

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Cite

BibTeXRIS
BibTeX
@misc{qin2026selective,
  title = {{Selective Mono and Diborylation of Aromatic Pentafluorosulfanyl Compounds by iridium-catalyzed C–H Activation}},
  author = {Yibo Qin and Shoubhik Das and Abderrahmane Amgoune and Anis Tlili},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008391/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008391/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Selective Mono and Diborylation of Aromatic Pentafluorosulfanyl Compounds by iridium-catalyzed C–H Activation
AU  - Yibo Qin
AU  - Shoubhik Das
AU  - Abderrahmane Amgoune
AU  - Anis Tlili
PY  - 2026
DA  - 2026/09/07
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008391/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008391/v1
AB  - 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.
ER  -