Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives DOI
Jie Wang, Shan-Shan Wang,

Jun Xiao

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(83), P. 12495 - 12498

Published: Jan. 1, 2023

CF3-substituted imidoyl sulfoxonium ylides (TFISYs) are extraordinarily versatile and powerful synthons for use in cyclization chemistry that affords diverse N-heterocycles. We first reacted TFISYs as a two-atom synthon with readily available azoalkenes then subjected the products to metal-free formal (4+2) cycloaddition chemistry. This protocol features mild conditions broad substrate scope, is simple operate, provides highly functionalized trifluoromethylpyridazines widely found bioactive molecules.

Language: Английский

Rhodium(iii)-catalyzed regioselective C2-alkenylation of indoles with CF3-imidoyl sulfoxonium ylides to give multi-functionalized enamines using a migratable directing group DOI

Zuguang Yang,

Jianhua Tang, Chen Li

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 59(3), P. 318 - 321

Published: Dec. 7, 2022

A rhodium(III)-catalyzed regioselective C2-alkenylation of indoles for the construction α-CF3 substituted enamines has been developed, which utilizes CF3-imidoyl sulfoxonium ylides (TFISYs) as alkenylating agents first time. wide array indolyl- and trifluoromethyl-decorated enamine derivatives have assembled in moderate to good yields.

Language: Английский

Citations

18
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
Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF3-Imidoyl Sulfoxonium Ylides via Triple C–H Activation DOI

Xiaoyang Gao,

Ruirui Zhai,

Juting Liao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 657 - 662

Published: Jan. 7, 2025

A condition-controlled Rh(III)-catalyzed selective synthesis of CF3-substituted indoles and pyrido[2,1-a]isoindoles from 2-arylpyridines CF3-imidoyl sulfoxonium ylides has been developed. The Cp*Rh(MeCN)3(SbF6)2/HFIP system afforded via triple C–H activation, while the [Cp*RhCl2]2/MeCN condition selectively furnished through [4 + 1] annulation. notable advantages this developed method included readily available starting materials, broad substrate scope, excellent chemoselectivity. Importantly, several selected products showed promising antitumor activities.

Language: Английский

Citations

0
Rh(III)-catalyzed C–H/C–C activation of benzoylacetonitriles and cyclization with CF3-imidoyl sulfoxonium ylides to 3-trifluoromethyl-isoquinolones DOI

Zuguang Yang,

Pinyi Li,

Zhengkai Chen

et al.

Journal of Catalysis, Journal Year: 2023, Volume and Issue: 427, P. 115098 - 115098

Published: Aug. 19, 2023

Language: Английский

Citations

8
Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives DOI
Jie Wang, Shan-Shan Wang,

Jun Xiao

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(83), P. 12495 - 12498

Published: Jan. 1, 2023

CF3-substituted imidoyl sulfoxonium ylides (TFISYs) are extraordinarily versatile and powerful synthons for use in cyclization chemistry that affords diverse N-heterocycles. We first reacted TFISYs as a two-atom synthon with readily available azoalkenes then subjected the products to metal-free formal (4+2) cycloaddition chemistry. This protocol features mild conditions broad substrate scope, is simple operate, provides highly functionalized trifluoromethylpyridazines widely found bioactive molecules.

Language: Английский

Citations

8