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Org. Lett 04.24

Synthesis of Seven- and Eight-Membered Rings by a Brønsted Acid Catalyzed Cationic Carbocyclization of Biphenyl Embedded Enynes

Jaime Tostado , Ana Milián, Juan J. Vaquero, and Manuel A. Fernández-Rodríguez*

Org. Lett. 2024, ASAP
DOI: acs.orglett.4c00647

A Brønsted acid catalyzed cyclization of o-alkenyl-o′-alkynylbiaryls for the synthesis of biologically relevant dibenzo-fused medium-sized rings has been developed. The outcome of the cyclization is determined by the nature of the substituent at the alkyne, with arenes favoring seven-membered rings and alkyl substituents producing eight-membered rings. These reactions proceed via a vinyl cation, which is captured by water and, notably, by C-nucleophiles, such as electron-rich (hetero)arenes.

Mercedes Zurro

Mercedes Zurro de la Fuente

Senior Research Fellow

    • 2023: Assistant Professor, Universidad de Alcalá (Madrid)
    • 2022-2023: Senior Research Fellow , Talent Attraction Program of Community of Madrid-Type 2, Universidad de Alcalá (Madrid)
    • 2021-2021: Postdoctoral Researcher, ICIQ (Prof. Miquel A. Pericàs).
    • 2018-2020: «Ramón Areces» Researcher, Rijks Universiteit Groningen (Prof. Syuzanna Harutyunyan).
    • 2017-2018: Postdoctoral Researcher, Universidad Complutense de Madrid (Prof. Luis Sánchez).
    • 2016: Ph.D. WWU Münster / Universität Regensburg. (Prof. Dr. Olga García Mancheño) Chiral triazole-based anion-binding catalysts for the asymmetric dearomatization of N-heteroarenes.
    • 2011: Graduated at the Universidad Complutense de Madrid.