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Article

Functional-Group-Tolerant, Silver-Catalyzed N-N Bond Formation by Nitrene Transfer to Amines

Publicated to:Journal Of The American Chemical Society. 139 (6): 2216-2223 - 2017-02-15 139(6), DOI: 10.1021/jacs.6b08219

Authors: Maestre, Lourdes; Dorel, Ruth; Pablo, Oscar; Escofet, Imma; Sameera, W M C; Alvarez, Eleuterio; Maseras, Feliu; Mar Diaz-Requejo, M; Echavarren, Antonio M; Perez, Pedro J

Affiliations

Barcelona Inst Sci & Technol, ICIQ, Inst Chem Res Catalonia, Avgda Palsos Catalans,16, Tarragona 43007, Spain - Author
CSIC, Ctr Invest Cient Isla Cartuja, Inst Invest Quim, Avea Americo Vespucio 49, Seville 41092, Spain - Author
Hokkaido Univ, Fac Sci, Dept Chem, Kita Ku, North 10 West 8, Sapporo, Hokkaido 0600810, Japan - Author
Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain - Author
Univ Huelva, CIQSO Ctr Invest Quim Sostenible, Unidad Asociada CSIC, Lab Catalisis Homogenea, Huelva 21007, Spain - Author
Univ Huelva, Dept Quim, Huelva 21007, Spain - Author
Univ Rovira & Virgili, Dept Quim Organ & Analit, C Marcelli Domingo S-N, Tarragona 43007, Spain - Author
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Abstract

Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI¿NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N bond formation were exclusively formed. Theoretical mechanistic studies have shown that this selective N-amidation reaction proceeds through triplet silver nitrenes.

Keywords

AminesBond formationSilver

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Journal Of The American Chemical Society 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, 2017, it was in position 8/171, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Multidisciplinary. Notably, the journal is positioned above the 90th percentile.

From a relative perspective, and based on the normalized impact indicator calculated from World Citations provided by WoS (ESI, Clarivate), it yields a value for the citation normalization relative to the expected citation rate of: 1.23. This indicates that, compared to works in the same discipline and in the same year of publication, it ranks as a work cited above average. (source consulted: ESI Nov 14, 2024)

This information is reinforced by other indicators of the same type, which, although dynamic over time and dependent on the set of average global citations at the time of their calculation, consistently position the work at some point among the top 50% most cited in its field:

  • Weighted Average of Normalized Impact by the Scopus agency: 1.91 (source consulted: FECYT Feb 2024)
  • Field Citation Ratio (FCR) from Dimensions: 7.04 (source consulted: Dimensions Jun 2025)

Specifically, and according to different indexing agencies, this work has accumulated citations as of 2025-06-18, the following number of citations:

  • WoS: 55
  • Scopus: 65
  • Europe PMC: 5
  • OpenCitations: 67

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 2025-06-18:

  • 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: 71.
  • 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: 71 (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: 5.85.
  • The number of mentions on the social network X (formerly Twitter): 10 (Altmetric).

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.
  • Assignment of a Handle/URN as an identifier within the deposit in the Institutional Repository: http://hdl.handle.net/20.500.11797/imarina3654708

Leadership analysis of institutional authors

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