Synthesis of highly substituted 1,3-dienes through halonium promoted 1,2-sulfur migration of propargylic thioethers

Martínez-Núñez, Clara; Velasco, Noelia; Sanz, Roberto; Suárez-Pantiga, Samuel

doi:10.1039/d3cc06194a

Chem. Commun.

2024

DOI: 10.1039/d3cc06194a

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Synthesis of highly substituted 1,3-dienes through halonium promoted 1,2-sulfur migration of propargylic thioethers

Clara Martínez-Núñez,

Noelia Velasco,

Roberto Sanz

et al.

Abstract: Conjugated 1-bromo or 1-iodo-1,3-dienes bearing a sulfide substituent have been synthesized via 1,2-sulfur migration from propargylic thioethers upon activation with NIS or NBS. The reaction generally proceeds with high control...

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2024

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Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations

Marín‐Díaz,

Martínez‐Núñez,

Sanz

et al. 2024

Eur J Org Chem

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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.

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Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations

Marín‐Díaz,

Martínez‐Núñez,

Sanz

et al. 2024

Eur J Org Chem

Self Cite

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Synthesis of highly substituted 1,3-dienes through halonium promoted 1,2-sulfur migration of propargylic thioethers

Abstract: Conjugated 1-bromo or 1-iodo-1,3-dienes bearing a sulfide substituent have been synthesized via 1,2-sulfur migration from propargylic thioethers upon activation with NIS or NBS. The reaction generally proceeds with high control...

Cited by 1 publication

References 48 publications

Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations

Halogen Promoted Desulfurative Cleavage of Cyclopropylmethyl Thioethers and Amination of the Formed Cyclopropylcarbinyl Cations

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