RT info:eu-repo/semantics/article
T1 Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations
A1 Marín Díaz, Pablo
A1 Martínez Núñez, Clara
A1 Sanz Díez, Roberto
A1 Suárez Pantiga, Samuel
K1 Química
K1 Chemistry
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB Wiley
SN 1434-193X
YR 2024
FD 2024-03
LK http://hdl.handle.net/10259/10503
UL http://hdl.handle.net/10259/10503
LA eng
NO 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
DS Repositorio Institucional de la Universidad de Burgos
RD 30-may-2025