Author, as appears in the article.: Dominguez-Molano, P; Weeks, R; Maza, RJ; Carbó, JJ; Fernández, E
Department: Química Física i Inorgànica
URV's Author/s: Carbó Martin, Jorge Juan / Domínguez Molano, Paula / Fernández Gutiérrez, Maria Elena / Maza Quiroga, Ricardo José
Keywords: Mechanism Dft calculations Copper Boryl-migration Alkylidenecyclobutanes
Abstract: Regioselective borylcupration of borylated skipped (Z)-dienes generates diborylated alkylcopper species that are involved in an intramolecular stereospecific B/Cu 1,3-rearrangement by migration of Bpin moiety from C(sp2) to C(sp3). DFT mechanistic studies showed that boryl migration occurs through the formation of 4-membered boracycle intermediate with a moderate free-energy barrier. Moreover, the use of KOMe forms stable Lewis base adducts with Bpin moieties that blocks the reaction. Subsequently to the 1,3-boron shift, the in situ electrophilic trapping allows selective C−H, C−C and C−X bonds, followed by intramolecular cross coupling giving access to cyclic functionalized alkylidenecyclohexanes or alkylidenecyclobutanes.
Thematic Areas: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: paula.dominguez@urv.cat paula.dominguez@urv.cat ricardojose.maza@estudiants.urv.cat ricardojose.maza@estudiants.urv.cat j.carbo@urv.cat mariaelena.fernandez@urv.cat
Author identifier: 0000-0002-3945-6721 0000-0001-9025-1791
Record's date: 2024-08-03
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202304791
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Angewandte Chemie (International Ed. Print). 62 (30): e202304791-
APA: Dominguez-Molano, P; Weeks, R; Maza, RJ; Carbó, JJ; Fernández, E (2023). Boron-Copper 1,3-Rearrangement: the New Concept Behind the Boryl Migration from C(sp2) in Alkenyl Boranes to C(sp3). Angewandte Chemie (International Ed. Print), 62(30), e202304791-. DOI: 10.1002/anie.202304791
Article's DOI: 10.1002/anie.202304791
Entity: Universitat Rovira i Virgili
Journal publication year: 2023
Publication Type: Journal Publications
Repositori URV