{rfName}
Ac

Indexed in

License and Use

Icono OpenAccess

Altmetrics

Analysis of institutional authors

Besora, MariaAuthorCarbo, Jorge JAuthorFernandez, ElenaAuthor

Share

June 10, 2025
Publications
>
Article
No

Access to amidines via C(sp2)-N coupling of trifluoroborate-iminiums with N-fluorobenzenesulfonimide

Publicated to: Chemical Science. 16 (26): 12012-12023 - 2025-06-03 16(26), DOI: 10.1039/d5sc02912k

Authors: Knez D; Šterman A; Sosič I; Perdih F; Nuñez GD; Knaflič T; Arčon D; Besora M; Carbó JJ; Fernández E; Časar Z

Affiliations

Inst Protect Cultural Heritage Slovenia, Res Inst, Poljanska Cesta 40, Ljubljana 1000, Slovenia - Author
Jozef Stefan Inst, Condensed Matter Phys Dept, Jamova Cesta 39, Ljubljana 1000, Slovenia - Author
Sandoz Dev Ctr Slovenia, Lek Pharmaceut Dd, Verovskova Ul 57, Ljubljana 1526, Slovenia - Author
Univ Ljubljana, Fac Chem & Chem Technol, Vecna Pot 113, Ljubljana 1000, Slovenia - Author
Univ Ljubljana, Fac Math & Phys, Jadranska 19, Ljubljana 1000, Slovenia - Author
Univ Ljubljana, Fac Pharm, Askerceva Cesta 7, Ljubljana 1000, Slovenia - Author
Univ Rovira i Virgili, Dept Quim Fis & Inorgan, 43007 Tarragona, Spain - Author
See more

Abstract

Amidines are an important class of organic compounds with widespread application as superbases, nucleophilic catalysts, and building blocks of heterocyclic compounds in organic synthesis. Moreover, they represent an important structural motif in medicinal chemistry. This work describes an application of primary trifluoroborate-iminiums in unprecedented azide- and transition-metal-free transformation to N-sulfonyl amidines in the presence of N-fluorobenzenesulfonimide (NFSI). This novel C(sp2)-N bond-forming reaction proceeds without excess of any reagent, under mild conditions and provides good to high yields of N-sulfonyl amidines by a simple isolation procedure. Density functional theory (DFT) mechanistic studies into this novel transformation support that the use of a base is required to activate either the trifluoroborate-iminium or the NFSI and promote the C(sp2)-N bond formation via nucleophilic attack of the nitrogen. The utility of the developed methodology is showcased with the synthesis of two bioactive compounds.

Keywords

AcidArylamidinesCarboxamidesDerivativesDesignEfficient synthesisInhibitorPotentSulfonamideSulfonyl formamidines

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Chemical Science due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2025, it was in position 43/239, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Multidisciplinary.

Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-12-09:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 1.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 1 (PlumX).

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 1.

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.

Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: Slovenia.

Awards linked to the item

This work was supported by the Slovenian Research and Innovation Agency (research programmes P1-0208, P1-0230, P1-0125, and PhD grant to A. S.). We also thank grant PID2021-128128NB-I00 and PID2022-141693NB-I00 funded by MINECO/AEI/10.13039/501100011033 and by "ERDF A way of making Europe" and the Generalitat de Catalunya (2021SGR00110). Authors acknowledge Mrs M. Frelih and Dr S. Pajk for HRMS analyses. Authors thank Prof. Dr S. Stavber, Dr M. Crnugelj and Dr A. Meden for valuable discussions.