2026-06-19T15:58:21Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/105032025-05-28T00:05:25Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Marín Díaz, Pablo Martínez Núñez, Clara Sanz Díez, Roberto Suárez Pantiga, Samuel 2025-05-27T12:23:40Z 2025-05-27T12:23:40Z 2024-03 1434-193X http://hdl.handle.net/10259/10503 10.1002/ejoc.202400147 1099-0690 Cyclopropylmethyl sulfides react with N-fluorosulfonimide (NFSI) or molecular iodine, enabling C−S cleavage to generate cyclopropylcarbinyl cations, which evolve through cyclopropane ring-opening reactions into homoallyl cations suitable to react with nucleophiles present in the reaction media. This desulfurative cleavage of cyclopropylmethyl thioethers under non-acidic conditions facilitates homoallylation of N-based nucleophiles such as alkyl or aryl amines as well as sulfonimides through a one-pot protocol in one or two steps depending on the nucleophile. The reaction is initiated by a halogen-sulfur bond that causes C−S bond cleavage. Moreover, the reaction with iodine proceeds through homoallyl iodide intermediates. We gratefully acknowledge Ministerio de Ciencia e Innovación (PID2020-115789GB-C21/AEI/10.13039/501100011033), and Junta de Castilla y León and FEDER (BU028P23) for financial support. C.M.-N. thanks Junta de Castilla y León for a predoctoral contract. S.S.-P. thanks a Ramón y Cajal (RYC2021-031533-I) contract funded by MCIN/AEI/10.13039/501100011033 and European Union “NextGenerationEU”/PRTR application/pdf eng Wiley European Journal of Organic Chemistry. 2024, V. 27, n. 20, p. e202400147 https://doi.org/10.1002/ejoc.202400147 Atribución-NoComercial 4.0 Internacional http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess Química Chemistry Química orgánica Chemistry, Organic Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion European Journal of Organic Chemistry 27 20 e202400147