Mild Strategy for the Preparation of Alkyl Sulfonyl Fluorides from Alkyl Bromides and Alcohols Using Photoredox Catalysis and Flow Chemistry DOI
Alejandro Gutiérrez‐González, Staffan Karlsson, Daniele Leonori

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3972 - 3976

Published: April 25, 2024

Facile access to sp3-rich scaffolds containing a sulfonyl fluoride group is still limited. Herein, we describe mild and scalable strategy for the preparation of alkyl fluorides from readily available bromides alcohols using photoredox catalysis. This approach based on halogen atom transfer (XAT), followed by SO2 capture fluorination. The method features conditions enabling fast high-value derivatives has been scaled up 5 g continuous stirred tank reactor cascade.

Language: Английский

Switchable carbo-fluorosulfonylation and hydro-fluorosulfonylation of alkenes enabled by bifunctional fluorosulfonyl radical precursors DOI Creative Commons

Ting Xiong,

Qilong Chen, Zhida Chen

et al.

Chem Catalysis, Journal Year: 2023, Volume and Issue: 3(12), P. 100821 - 100821

Published: Nov. 28, 2023

Language: Английский

Citations

13
Photoredox-catalyzed intermolecular azidosulfonylation of alkenes with DABCO·(SO2)2, trimethylsilyl azide and thianthrenium salts DOI

Huiling Ma,

Yanzhi Li, Peiqi Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(4), P. 866 - 871

Published: Dec. 21, 2022

Synthesis of β-azido alkylsulfones through a photoredox-catalyzed azido sulfonylation alkenes with DABCO·(SO 2 ) , trimethylsilyl azide and alkyl thianthrenium salts is developed.

Language: Английский

Citations

21
Radical Fluorosulfonyl Arylation of Alkenes: Accessing FSO2-Functionalized Chromanes via Formal Endo and Exo Cyclization DOI
Honghai Zhang,

Na Yang,

Jing Li

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(44), P. 8170 - 8175

Published: Oct. 31, 2022

The introduction of sulfonyl fluoride groups into bioactive molecules can often bring about enhanced biological activity, which has attracted more research interest in chemical biology and drug development recent years. Here, we report the a radical fluorosulfonylation alkenes/intramolecular arylation cascade for construction chromanes with attached. 1,2-fluorosulfonyl reactions proceed well both endo exo cyclization fashions, allowing further variation distance between chromane core group.

Language: Английский

Citations

19
C(sp3)–H fluorosulfonylvinylation/aza-Michael addition approach to FSO2-functionalized tetrahydropyridines DOI
Shuai Shi, Xueyan Zhao, Dengfeng Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3805 - 3810

Published: Jan. 1, 2023

We have developed an efficient approach for the synthesis of FSO 2 -functionalized tetrahydropyridines from propargyl alcohols, Cl, and anilines.

Language: Английский

Citations

12
Mild Strategy for the Preparation of Alkyl Sulfonyl Fluorides from Alkyl Bromides and Alcohols Using Photoredox Catalysis and Flow Chemistry DOI
Alejandro Gutiérrez‐González, Staffan Karlsson, Daniele Leonori

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3972 - 3976

Published: April 25, 2024

Facile access to sp3-rich scaffolds containing a sulfonyl fluoride group is still limited. Herein, we describe mild and scalable strategy for the preparation of alkyl fluorides from readily available bromides alcohols using photoredox catalysis. This approach based on halogen atom transfer (XAT), followed by SO2 capture fluorination. The method features conditions enabling fast high-value derivatives has been scaled up 5 g continuous stirred tank reactor cascade.

Language: Английский

Citations

4