2026-04-21T08:58:19Zhttps://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 bbff6ac0-7c8f-42bb-897d-add4b0198aaa 600 Martínez Núñez, Clara 823 600 Sanz Díez, Roberto 531 600 0000-0003-2830-0892 Suárez Pantiga, Samuel 544 600 0000-0002-4249-7807 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 THUMBNAIL Marín-ejooc_2024.pdf.jpg Marín-ejooc_2024.pdf.jpg IM Thumbnail image/jpeg 4824 https://riubu.ubu.es/bitstream/10259/10503/4/Mar%c3%adn-ejooc_2024.pdf.jpg 8e2c9711cc6f8398aac87c7d30604b92 MD5 4 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/10503/3/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 3 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 914 https://riubu.ubu.es/bitstream/10259/10503/2/license_rdf 24013099e9e6abb1575dc6ce0855efd5 MD5 2 ORIGINAL Marín-ejooc_2024.pdf Marín-ejooc_2024.pdf application/pdf 3684255 https://riubu.ubu.es/bitstream/10259/10503/1/Mar%c3%adn-ejooc_2024.pdf fa74c6cc0c8126a61cf92005402f581e MD5 1 10259/10503 oai:riubu.ubu.es:10259/10503 2025-05-28 02:05:25.673 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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