Construction of trifluoromethyl-substituted enaminones via rhodium(III)-catalyzed aldehydic C(sp2)–H bond activation of N-sulfonyl-2-aminobenzaldehydes with CF3-imidoyl sulfoxonium ylides DOI

Yubo Duan,

Zhaolin Quan,

Zhengkai Chen

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: unknown, P. 134408 - 134408

Published: Dec. 1, 2024

Language: Английский

Three-component synthesis ofN-naphthyl pyrazolesviaRh(iii)-catalyzed cascade pyrazole annulation and Satoh–Miura benzannulation DOI

Demao Chen,

Liyun Zhou,

Yunyun Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(27), P. 4036 - 4039

Published: Jan. 1, 2023

The synthesis of N-naphthyl pyrazoles has been realized by the direct three-component reactions enaminones, aryl hydrazine hydrochlorides and internal alkynes via Rh(III) catalysis. synthetic employing simple substrates lead to simultaneous construction dual cyclic moieties, including a pyrazole ring phenyl ring, sequential formation two C-N three C-C bonds.

Language: Английский

Citations

33
Chameleonic Reactivity of Imidoyl Sulfoxonium Ylides: Access to Functionalized Pyrroles and Dihydro-pyridines DOI
Jingnan Xu,

Ren‐Yin Yang,

Bo Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(1), P. 62 - 67

Published: Jan. 3, 2024

We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, ylides react with electron-deficient reagents, such as alkynyl esters, to lead formation 1,2-dihydro-pyridines. The methyl group attached sulfur atom acts methylene donor. other pyridinium 1,4-zwitterionic thiolates, which leads functionalized pyrroles. Both transformations feature mild reaction conditions and good functional tolerance.

Language: Английский

Citations

9
Synthesis of CF3–Isoquinolinones and Imidazole-Fused CF3–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines DOI

Miaomiao Liang,

Shengnan Yan,

Yuanshuang Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10180 - 10196

Published: July 4, 2024

Presented herein are novel syntheses of CF

Language: Английский

Citations

9
Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives DOI

Zuguang Yang,

Guangming Wei,

Zhengkai Chen

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(33), P. 4872 - 4890

Published: Jan. 1, 2023

Recent advances in the direct synthesis of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides (TFAICs) and derivatives, including trifluoroacetimidohydrazides (TFAIHs) CF3-imidoyl sulfoxonium ylides (TFISYs), are systematically summarized discussed. The cascade annulation reactions synthons with suitable coupling partners have emerged as a powerful promising tool for construction variety trifluoromethyl-substituted heterocycles. Compared other building blocks, TFAICs derivatives notable merits easy availability handling, relative stability safety, high reactivity.

Language: Английский

Citations

22
Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones DOI

Yubo Duan,

Shu‐Ning Lu,

Zuguang Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3843 - 3848

Published: Jan. 1, 2023

We have developed a Rh( iii )-catalyzed C–H activation/chemodivergent annulation of N -carbamoylindoles with TFISYs, allowing facile access to variety trifluoromethyl-substituted (dihydro)pyrimidoindolones high efficiency. Solvents play critical role in the selectivity reaction.

Language: Английский

Citations

22
Synthesis of 5‐Trifluoromethyl‐1,4‐dihydro‐1,2,4‐triazines via Base‐mediated [3+3] Cycloaddition of Nitrile Imines and CF3‐Imidoyl Sulfoxonium Ylides DOI
Yue Sun,

Sihao Ling,

Yubo Duan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1521 - 1525

Published: March 31, 2023

Abstract An approach for the construction of 5‐trifluoromethyl‐1,4‐dihydro‐1,2,4‐triazines has been developed via base‐mediated [3+3] cycloaddition in‐situ generated nitrile imines and CF 3 ‐substituted imidoyl sulfoxonium ylides. The metal‐free protocol is characterized by readily available starting materials, mild conditions, a broad substrate scope, high efficiency, good synthetic prospect, scalability. magnified image

Language: Английский

Citations

17
Synthesis of 5‐Trifluoromethylpyrroles from Heating‐Induced Annulation of Pyridinium 1,4‐Zwitterionic Thiolates with CF3‐Imidoyl Sulfoxonium Ylides DOI

Sihao Ling,

Yu Zhang, Zhengkai Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(19), P. 3382 - 3386

Published: Aug. 16, 2023

Abstract A heating‐induced desulfuration annulation of pyridinium 1,4‐zwitterionic thiolates and CF 3 ‐substituted imidoyl sulfoxonium ylides has been achieved, allowing a route to biologically important 5‐trifluoromethylpyrroles. The transformation proceeds through an unusual ((3+3)‐1) pathway under metal‐free conditions with the extrusion 4‐methoxypyridine, sulfur DMSO. scale‐up reaction further obtained pyrrole products have performed demonstrate synthetic utility developed method.

Language: Английский

Citations

15
Rh(III)‐Catalyzed Cascade Cyclization of 2‐Aryl‐3H‐indoles and CF3‐Imidoyl Sulfoxonium Ylides Toward Trifluoroacetimidoyl‐Substituted 11H‐Isoindolo[2,1‐a]indoles DOI Creative Commons

Zuguang Yang,

pinyi li,

Zhengkai Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3855 - 3860

Published: Oct. 18, 2023

Abstract A rhodium(III)‐catalyzed C−H activation/[4+1] annulation of 2‐aryl‐3 H ‐indoles and CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs) has been achieved, producing a wide variety trifluoroacetimidoyl‐substituted 11 ‐isoindolo[2,1‐a]indoles in 51–86% yields. The cascade reaction involves imidoylmethylation, tautomerization AgOAc‐mediated C−N bond formation sequence. could be scaled up to 2 mmol scale.

Language: Английский

Citations

14
Synthesis of 2‐Trifluoromethyl‐4‐aminoquinolines via Heating‐Promoted Multi‐component Reaction of CF3‐Imidoyl Sulfoxonium Ylides and Amines with Difluorocarbene as a C1 Synthon† DOI Creative Commons

Guangming Wei,

Chen Li, Hao‐Yuan Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(23), P. 3205 - 3210

Published: July 17, 2023

Comprehensive Summary A thermally‐induced multi‐component reaction of CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs), amines and (triphenylphosphonio)difluoroacetate (PDFA) has been developed, allowing a facile access to 2‐trifluoromethyl‐4‐aminoquinolines in high yields. The proceeds smoothly with or without the addition sulfur utilizes difluorocarbene as C1 synthon under simply heating conditions. Mechanistic study reveals that in‐situ generated thiocarbonyl fluoride, isothiocyanate gem ‐difluoroalkene might act key intermediates.

Language: Английский

Citations

13
Divergent Synthesis of Trifluoromethyl-Substituted 1,2-Dihydroquinoxalines and Diimines by Cascade Reactions of CF3–Imidoyl Sulfoxonium Ylides with Azo Compounds DOI

Guangming Wei,

Dongling Zheng,

Chen Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(38), P. 7046 - 7050

Published: Sept. 18, 2023

A base-mediated cascade reaction of CF3-imidoyl sulfoxonium ylides and azo compounds has been achieved, allowing for facile access to trifluoromethyl-substituted 1,2-dihydroquinoxalines diimines in moderate excellent yields. Noteworthy is that the unusual N-N bond cleavage rearrangement are involved transformations.

Language: Английский

Citations

11