Monofluoromethylation of Cyclic Sulfamidates and Sulfates with a-Fluorocarbanions of Fluorobis(phenylsulfonyl)methane and Ethyl 2-Fluoroacetoacetate - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2023

Monofluoromethylation of Cyclic Sulfamidates and Sulfates with a-Fluorocarbanions of Fluorobis(phenylsulfonyl)methane and Ethyl 2-Fluoroacetoacetate

Jun‐liang Zeng
Liangfeng Niu
  • Fonction : Auteur
Zhiwen Wang
  • Fonction : Auteur
Renjie Wei
  • Fonction : Auteur

Résumé

A regioselective fluoromethylation by ring-opening of cyclic sulfamidates and sulfates with a-fluorocarbanions and subsequent reductive desulfonylation is developed. Fluorobis(phenylsulfonyl)methane (FBSM) was explored as fluoromethide equivalent and the reaction was extended to the afluorocarbanion of ethyl 2-fluoroacetoacetate. This approach allows access to g-and d-fluoroamines as well as g-and d-fluoroalcohols in high yields.

Domaines

Chimie
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Dates et versions

hal-04234760 , version 1 (10-10-2023)

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Citer

Jun‐liang Zeng, Liangfeng Niu, Zhiwen Wang, Renjie Wei, Dominique Cahard. Monofluoromethylation of Cyclic Sulfamidates and Sulfates with a-Fluorocarbanions of Fluorobis(phenylsulfonyl)methane and Ethyl 2-Fluoroacetoacetate. European Journal of Organic Chemistry, 2023, 26 (38), ⟨10.1002/ejoc.202300651⟩. ⟨hal-04234760⟩
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