Intermolecular Defluorinative 1,2-Diamination of Fluoroalkenyl Iodides with Sulfonamides: Synthesis of Acyclic and Cyclic Fluorinated 1,2-Enediamines

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

An intermolecular defluorinative vicinal diamination protocol employing fluoroalkenyl iodides and sulfonamides for the efficient synthesis of a series acyclic cyclic fluorinated 1,2-enediamines has been developed.

Язык: Английский

1,2‐Dichloroethane‐Assisted Defluorinative Ring‐Opening Reaction of DABCO and Polyfluoroalkyl Peroxides: Synthesis of Fluorinated N‐Ethyl Piperazines

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 14, 2024

Comprehensive Summary A catalyst‐free and additive‐free ring‐opening reaction of polyfluoroalkyl peroxides, triethylenediamine (DABCO), 1,2‐dichloroethane (DCE) has been developed for the defluorinative synthesis structurally diverse piperazines featuring a fluoroenone framework N ‐chloroethyl‐substituent with high Z ‐stereoselectivity. The success this three‐component is attributed to in situ generation an active 1‐(2‐chloroethyl)‐1,4‐diazabicyclo[2.2.2]octan‐1‐ium (DABCO·DCE) salt, which judiciously acts as formal ‐(2‐chloroethyl)piperazine equivalent coupling less‐studied aliphatic fluorinated substances. Impressively, accomplishes multi‐activation robust C(sp 3 )‐F, )‐Cl, )‐O, )‐N bonds one‐pot process, offering practical platform late‐stage functionalization complex molecules. Furthermore, resulting products can not only serve versatile building blocks heterocycles, but also undergo C—Cl bond displacement transformations ‐, O S ‐nucleophiles.

Язык: Английский

Transition-metal-free defluorinative cyclization of perfluoroalkyl alkenyl iodides with C,N-dinucleophiles: synthesis of (E)-perfluoroalkenyl pyrroles

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 1, 2024

Язык: Английский