Photoredox Catalytic Defluoroalkylation of gem-Difluoroalkenes with Secondary N-Alkylanilines via C–F/C–H Coupling DOI
Hai Hu,

Baokai Yang,

Yifan Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 22, 2024

To provide fluorinated allylamines, a visible-light photocatalytic C–F/C–H coupling of easily accessible gem-difluoroalkenes and secondary N-alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility broad scope including complex natural product derivatives, thus providing green method for the preparation high-value functionalized monofluoroalkenes. Mechanistic studies elucidated photoredox catalyzed radical–radical pathway.

Language: Английский

Selectivity in Rh-catalysis with gem-difluorinated cyclopropanes DOI
Yaxin Zeng, Zhong‐Tao Jiang, Ying Xia

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(28), P. 3764 - 3773

Published: Jan. 1, 2024

This feature article summarizes our efforts towards developing Rh-catalyzed reactions of gem -difluorinated cyclopropanes, briefly discussing the design, selectivity, mechanisms and future research prospects.

Language: Английский

Citations

12
Palladium-Catalyzed Cross-Coupling of gem-Difluorocyclopropanes with gem-Diborylalkanes for the Synthesis of Boryl-Substituted Fluorinated Alkenes DOI
Ebrahim‐Alkhalil M. A. Ahmed,

Hongchen Zhang,

Wen-Gen Cao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 9020 - 9024

Published: Dec. 8, 2023

This study presents a novel method for the regioselective coupling of gem-difluorinated cyclopropanes with gem-diborylmethane, utilizing Pd-catalyst system. innovative approach enables synthesis 2-fluoroalkenyl monoboronate scaffolds high Z-selectivity. The resulting products undergo further transformations, including oxidation, Suzuki cross-coupling, and trifluoroborylation, all which are achieved good yields. work introduces valuable synthetic pathway to access important fluorinated compounds various applications in organic chemistry.

Language: Английский

Citations

14
Double strain-release enables formal C–O/C–F and C–N/C–F ring-opening metathesis DOI Creative Commons

Yulei Zhu,

Jie Jia,

Xiangyu Song

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13800 - 13806

Published: Jan. 1, 2024

Metathesis reactions have been established as a powerful tool in organic synthesis. While great advances were achieved double-bond metathesis, like olefin metathesis and carbonyl single-bond has received less attention the past decade. Herein, we describe first C(sp

Language: Английский

Citations

5
Palladium-catalyzed cross-coupling of gem-difluorocyclopropanes with gem-diborylalkanes: facile synthesis of a diverse array of gem-diboryl-substituted fluorinated alkenes DOI Creative Commons
Ebrahim‐Alkhalil M. A. Ahmed,

Hongchen Zhang,

Wen-Gen Cao

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(13), P. 10265 - 10272

Published: Jan. 1, 2025

This study introduces an efficacious palladium-catalyzed method for the regioselective and stereoselective cross-coupling of gem -difluorinated cyclopropanes with array -diborylalkanes under mild reaction conditions.

Language: Английский

Citations

0
Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes DOI

Zimin Wang,

Daniel C. Hong,

Hongfang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-difluorocyclopropanes with structurally diverse (hetero)arylsilanes through C-C bond activation and C-F cleavage. This regioselective features a broad substrate scope excellent functional group compatibility, affording variety linear 2-fluoroallylic scaffolds in good yields high Z-selectivity.

Language: Английский

Citations

0
CO2 and palladium enabled highly chemoselective hydroxylation of gem-difluorocyclopropanes DOI Creative Commons

Xingben Wang,

Fang Xiao, Frédéric W. Patureau

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2494 - 2501

Published: Jan. 1, 2024

A mild chemoselective CO 2 and palladium mediated hydroxylation method of gem -difluorocyclopropanes is herein reported, in the presence water. broad functional group tolerance multiple mechanistic experiments are described discussed.

Language: Английский

Citations

3
Pd-IHept-Catalyzed Ring-Opening of gem-Difluorocyclopropanes with Malonates Via Selective C–C Bond Cleavage: Synthesis of Monofluoroalkenes DOI
Yuxuan Yan, Huijun Qian, Leiyang Lv

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(22), P. 16253 - 16261

Published: Sept. 22, 2023

Monofluoroalkene scaffolds are frequently found in various functional molecules. Herein, we report a Pd-IHept-catalyzed (NHC = N-heterocyclic carbene) defluorinative functionalization approach for the synthesis of monofluoroalkenes from

Language: Английский

Citations

7
Pd-Catalyzed Ring-Opening of gem-Difluorocyclopropanes for the Mono- and Bis-fluoroallylation of 1,3-Dicarbonyls DOI
Yuxuan Yan,

Wanqing Lu,

Huijun Qian

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1630 - 1630

Published: Jan. 1, 2024

Language: Английский

Citations

2
Photoredox Catalytic Defluoroalkylation of gem-Difluoroalkenes with Secondary N-Alkylanilines via C–F/C–H Coupling DOI
Hai Hu,

Baokai Yang,

Yifan Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 22, 2024

To provide fluorinated allylamines, a visible-light photocatalytic C–F/C–H coupling of easily accessible gem-difluoroalkenes and secondary N-alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility broad scope including complex natural product derivatives, thus providing green method for the preparation high-value functionalized monofluoroalkenes. Mechanistic studies elucidated photoredox catalyzed radical–radical pathway.

Language: Английский

Citations

0