Aminofluorosulfonylation of β,γ-Unsaturated Hydrazones with Sulfur Dioxide and N-Fluorobenzenesulfonimide: Accessing Pyrazoline-Functionalized Aliphatic Sulfonyl Fluorides DOI

Zhi-Min Yan,

Qi Lin,

Tong-Yang Cao

и другие.

Organic Letters, Год журнала: 2023, Номер 25(21), С. 3910 - 3915

Опубликована: Май 24, 2023

An efficient aminofluorosulfonylation strategy was developed for the synthesis of various pyrazoline-functionalized aliphatic sulfonyl fluorides using β,γ-unsaturated hydrazones with sulfur dioxide and NFSI as starting materials under mild conditions. The fluoride products could be successfully transformed into corresponding sulfonate esters amides via sulfur(VI) exchange (SuFEx) click reactions. Preliminary mechanistic investigations demonstrate that reaction operates through a radical cyclization/SO2 insertion/fluorination cascade process.

Язык: Английский

Modular synthesis of functional libraries by accelerated SuFEx click chemistry DOI Creative Commons
Joshua A. Homer, Rebecca A. Koelln, Andrew S. Barrow

и другие.

Chemical Science, Год журнала: 2024, Номер 15(11), С. 3879 - 3892

Опубликована: Янв. 1, 2024

The Accelerated SuFEx Click Chemistry (ASCC) protocol, adapted to a 96-well plate format, has been applied the late-stage derivatization of bioactive molecules and array synthesis anticancer agents, showcasing its potential for drug discovery.

Язык: Английский

Процитировано

6

Sulfur–Phenolate Exchange: SuFEx‐Derived Dynamic Covalent Reactions and Degradation of SuFEx Polymers DOI
Yang Chao, Akash Krishna, Muthusamy Subramaniam

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(36)

Опубликована: Июль 12, 2022

Abstract The products of the SuFEx reaction between sulfonimidoyl fluorides and phenols, sulfonimidates, are shown to display dynamic covalent chemistry with other phenols. This was be enantiospecific, finished in minutes at room temperature high yields, useful for both asymmetric synthesis sustainable polymer production. Its wide scope further extends usefulness related click chemistries.

Язык: Английский

Процитировано

25

Hydrosulfonylation of Unactivated Alkenes and Alkynes by Halogen-Atom Transfer (XAT) Cleavage of SVI–F Bond DOI
Wu Xing, Bing Gao

Organic Letters, Год журнала: 2023, Номер 25(48), С. 8722 - 8726

Опубликована: Ноя. 29, 2023

A photochemical halogen-atom transfer (XAT) method for generating sulfonyl radicals from aryl fluorides has been developed. It allows the hydrosulfonylation of unactivated alkenes, which was challenging to achieve through our previous single-electron route. This reaction excellent functional group tolerance and substrate scope under mild conditions.

Язык: Английский

Процитировано

16

Sulfur-fluoride exchange (SuFEx)-enabled lead discovery of AChE inhibitors by fragment linking strategies DOI
Ziwen Zhang,

Shilong Zhang,

Chengyao Wu

и другие.

European Journal of Medicinal Chemistry, Год журнала: 2023, Номер 257, С. 115502 - 115502

Опубликована: Май 18, 2023

Язык: Английский

Процитировано

13

Aminofluorosulfonylation of β,γ-Unsaturated Hydrazones with Sulfur Dioxide and N-Fluorobenzenesulfonimide: Accessing Pyrazoline-Functionalized Aliphatic Sulfonyl Fluorides DOI

Zhi-Min Yan,

Qi Lin,

Tong-Yang Cao

и другие.

Organic Letters, Год журнала: 2023, Номер 25(21), С. 3910 - 3915

Опубликована: Май 24, 2023

An efficient aminofluorosulfonylation strategy was developed for the synthesis of various pyrazoline-functionalized aliphatic sulfonyl fluorides using β,γ-unsaturated hydrazones with sulfur dioxide and NFSI as starting materials under mild conditions. The fluoride products could be successfully transformed into corresponding sulfonate esters amides via sulfur(VI) exchange (SuFEx) click reactions. Preliminary mechanistic investigations demonstrate that reaction operates through a radical cyclization/SO2 insertion/fluorination cascade process.

Язык: Английский

Процитировано

13