2-Amino-3,3-difluoro-2,3-dihydrofurans from Difluorocarbenes and Enaminones DOI

Synfacts, Journal Year: 2022, Volume and Issue: 18(06), P. 0605 - 0605

Published: May 17, 2022

Key words difluorodihydrofurans - difluorocarbenes cascade reaction enaminones

Language: Английский

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

Citations

63
Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene DOI
Yao Zhou,

F Chen,

Ziru Li

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(7), P. 1975 - 1981

Published: May 11, 2023

Language: Английский

Citations

29
Construction and transformations of 2,2-difluoro-2,3-dihydrofurans from enaminones and diflurocarbene DOI

Heyun Sheng,

Zhiwei Chen, Xue Li

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(11), P. 3000 - 3005

Published: Jan. 1, 2022

A simple and efficient construction of 2-difluoro-2,3-dihydrofurans is reported, which features metal-free additive-free conditions, high functional group tolerance readily accessible starting materials.

Language: Английский

Citations

27
Photoinduced Three‐Component Cyclization of Arylamines, Enaminones and Difluorobromoacetates to 2,3‐Difunctionalized Quinolines DOI
Jie Huo, Xiao Geng, Wanmei Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(20), P. 3539 - 3543

Published: Aug. 26, 2022

Abstract A photoinduced multicomponent reaction of arylamines, enaminones and difluorobromoacetates for the synthesis 2,3‐difunctionalized quinolines is reported. This strategy features broad functional groups tolerance wide substrate scopes that enables further synthetic applications obtained products. Mechanistic studies reveal intermolecular [3+3] cyclization between in‐situ generated 1,3‐vinylimine ions arylamines key step in this transformation. magnified image

Language: Английский

Citations

23
Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines DOI
Xiang Li, Qiwen Pang, Yang Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2607 - 2612

Published: Jan. 1, 2024

A metal-free, scalable, and cascade protocol for assembling diverse polysubstituted pyridines from tertiary enaminones α,β-unsaturated sulfonylketimines by cleaving C–N/N–S bonds is reported.

Language: Английский

Citations

4
Carbene-induced ring-opening reactions of five-/six-membered cyclic ethers: expanding the frontiers of functional group introduction and molecular architecture construction DOI
Jun Xiao,

Dandan Jiang,

Xiujuan Wu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The multi-component ring-opening reactions of cyclic ethers offer an efficient strategy for the rapid introduction multiple functional groups and construction complex molecular architectures.

Language: Английский

Citations

0
Mechanistic Insights on the Annulation of Difluorocarbene and Enaminones DOI
Shi Cheng, Chen Tian, Jiaxi Xu

et al.

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

Published: May 8, 2025

Computational studies on all proposed possible mechanisms of the annulations difluorocarbene and enaminones were carried out, providing comprehensive mechanistic insights into annulations. The results suggest that asynchronous concerted [4 + 1] cycloaddition is more favorable for annulation enaminones, leading to 2,2-difluoro-2,3-dihydrofuran-3-amine derivatives hardly 3,3-difluoro-2,3-dihydrofuran-2-amine derivatives, which even documented be obtained should minor products. calculation further verified experimentally. current provide a thorough understanding correct an unreasonable reported result.

Language: Английский

Citations

0
Iron-catalysed reductive coupling for the synthesis of polyfluorinated compounds DOI
Yu‐Qiu Guan,

Tian‐Zhang Wang,

Jia-Fan Qiao

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(100), P. 13915 - 13918

Published: Jan. 1, 2022

Herein we reported the use of Earth-abundant iron as catalytic metal in presence Mn to induce difluorobromoacetates form carbon radicals, which reacted with trifluoromethyl olefins followed by β-F elimination generate corresponding gem-difluoroolefins. The cross-electrophile coupling displayed excellent functional group tolerance and broad substrate scope under mild reductive conditions, affording a large number polyfluorinated compounds, could be further transformed other valuable molecules.

Language: Английский

Citations

16
Stereoselective synthesis of 1,3- and 1,4-dicarbonyl-alkenes from cyclopropenes in a catalytic zinc system DOI

Jia‐Bin Han,

Yu Liu,

Xiaoyan Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4887 - 4894

Published: Jan. 1, 2023

This work describes a dual catalytic system for selective synthesis of α-allyl-1,3-ketoaldehydes and α-vinyl-1,4-ketoaldehydes through cascade reactions hydroxyl substituted aromatic enaminones with cyclopropenes under zinc promoted conditions.

Language: Английский

Citations

8
Facile access to the 2,2-difluoro-2,3-dihydrofuran skeleton without extra additives: DMF-promoted difluorocarbene formation of ClCF2CO2Na DOI

Zunsheng Chen,

Xin Xie, Wei-Ming Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(41), P. 8037 - 8041

Published: Jan. 1, 2022

A practical and facile difluorocarbene-triggered cycloaddition reaction of enaminones was developed, which delivered 2,2-difluoro-2,3-dihydrofurans without any extra additives.

Language: Английский

Citations

13