December 25, 2023
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Article
Hybrid Gold

Nickel-Catalyzed Cycloisomerization of 1,5-Allenynes

Publicated to:ADVANCED SYNTHESIS & CATALYSIS. 366 (4): 790-797 - 2024-02-20 366(4), DOI: 10.1002/adsc.202301090

Authors: Nieto-Carmona, JC; Manjón-Mata, I; Quirós, MT; Caballero-Santiago, G; Pérez-Maseda, F; Cárdenas, DJ

Affiliations

Univ Alcala, Fac Farm, Dept Organ Chem & Inorgan Chem, Campus Univ Ctra Madrid Barcelona,Km 33,600 Alcala, Madrid 28871, Spain - Author
Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, Fac Ciencias, Dept Organ Chem, Red ORFEO CINQA Av Francisco Tomas & Valiente 7,Ca, Madrid 28049, Spain - Author
Universidad Autónoma de Madrid - Author
Universidad de Alcalá - Author

Abstract

We report the Ni-catalyzed cycloisomerization of 1,5-allenynes. Substrates containing terminal alkynes afford cyclopentene derivatives, whereas internal alkynes lead to the formation of two consecutive C−C bonds to give fused 5–5 bicyclic compounds. The reaction shows a wide scope. Experimental and computational mechanistic studies suggest a Ni(0)−Ni(II) catalytic cycle. The reaction starts with an oxidative cyclometallation followed by a β-hydrogen elimination. The trans arrangement of alkenyl and hydride ligands is key to allow formation of the second carbocycle.

Keywords

1,6-allenynesactivationalkyneallenynescyclizationdynamicsenyne-alleneshydroborylative cyclizationnickelreaction mechanismsreactivityrearrangementAllenesCyclizationNickelReaction mechanismsThermal c-2-c-6 cyclization

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal ADVANCED SYNTHESIS & CATALYSIS 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, 2024 there are still no calculated indicators, but in 2023, it was in position 19/74, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Applied.

From a relative perspective, and based on the normalized impact indicator calculated from the Field Citation Ratio (FCR) of the Dimensions source, it yields a value of: 1.48, which 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: Dimensions Jul 2025)

Specifically, and according to different indexing agencies, this work has accumulated citations as of 2025-07-20, the following number of citations:

  • Scopus: 4

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 2025-07-20:

  • 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: 2.

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: 1.25.
  • The number of mentions on the social network X (formerly Twitter): 4 (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: https://repositorio.uam.es/handle/10486/709381

Leadership analysis of institutional authors

There is a significant leadership presence as some of the institution’s authors appear as the first or last signer, detailed as follows: First Author (NIETO CARMONA, JUAN CARLOS) .