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

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
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 CF3-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site DOI

Manqing Wang,

Shengnan Yan,

Bin Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7828 - 7842

Published: May 22, 2024

Presented herein is a novel synthesis of CF

Language: Английский

Citations

6
Rhodium(III)-Catalyzed Coupling of Quinolin-8-carboxaldehydes with CF3–Imidoyl Sulfoxonium Ylides by Chelation-Assisted C(sp2)-H Bond Activation for the Synthesis of Trifluoromethyl-Substituted Enaminones DOI

Pinyi Li,

Zuguang Yang,

Zhengkai Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10736 - 10747

Published: July 18, 2024

A rhodium(III)-catalyzed aldehydic C(sp

Language: Английский

Citations

6
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
Rh(III)‐Catalyzed C‐H Cyclization of 2‐Arylbenzimidazoles with CF3‐Imidoyl Sulfoxonium Ylides and Further Sc(III)‐Catalyzed Deaminative Hydroxylation DOI Open Access

Juting Liao,

Ruirui Zhai,

Xiaoyang Gao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 16, 2024

Abstract An efficient Rh(III)‐catalyzed C−H bond activation/cyclization of 2‐arylbenzimidazoles with CF 3 ‐imidoyl sulfoxonium ylides has been achieved, yielding diverse − and amino‐disubstituted 5,6‐dihydrobenzoimidazo[2,1‐ a ]isoquinolines, which could undergo deaminative hydroxylation to access hydroxy‐disubstituted ]isoquinolines catalyzed by Sc(OTf) . This developed strategy features easily available starting materials, broad substrate scope, good scalability high efficiency. Moreover, the antitumor activities selected products against some human cancer cell lines were also investigated, results indicated that several show antiproliferative activities.

Language: Английский

Citations

4
Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF3−Imidoyl Sulfoxonium Ylides DOI
Yue Sun,

Sihao Ling,

Zhengkai Chen

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 29, 2024

Abstract A metal‐free [4+1] annulation of in‐situ generated ortho ‐quinone methides ( o ‐QMs) and CF 3 −imidoyl sulfoxonium ylides (TFISYs) has been achieved under mild conditions, which provides a facile straightforward access to variety trifluoromethyl‐containing 2,3‐dihydrobenzofurans in moderate excellent yields.

Language: Английский

Citations

3
Synthesis of CF3-Indazoles via Rh(III)-Catalyzed C-H [4+1] Annulation of Azobenzenes with CF3-Imidoyl Sulfoxonium Ylides DOI Creative Commons
Yongjia Shang, Chen Li,

Guiqiu Wang

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(1), P. 183 - 183

Published: Jan. 5, 2025

An efficient Rh(III)-catalyzed C-H activation of azobenzenes and subsequent [4+1] cascade annulation with CF3-imidoyl sulfoxonium ylides was developed, yielding diverse CF3-indazoles. This protocol featured easily available starting materials, excellent functional group tolerance high efficiency. Moreover, the antitumor activities selected CF3-indazoles against human cancer cell lines were also studied, results indicated that several compounds displayed considerable antiproliferative activities.

Language: Английский

Citations

0