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

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 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
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
A Regioselective Ruthenium‐Catalyzed Oxidative C–H Alkenylation of 2‐Aryl‐4H‐Benzo[d][1,3] Oxazin‐4‐Ones DOI

Sepideh Bahrami Nasab,

Seyed Iman Alavioon

Applied Organometallic Chemistry, Journal Year: 2025, Volume and Issue: 39(6)

Published: May 2, 2025

ABSTRACT 2‐Aryl‐ 4H ‐benzo[ d ][ 1 , 3 ]oxazin‐ 4 ‐one derivatives can be directly alkenylated with alkyl acrylates using a facile Ru (II)‐catalyzed process; Cu (OAc) 2 •H O as an oxidizer through formation of pentagon cyclic complex imine‐Ru (II) for C–H activation is described. The unique catalytic reaction well matched miscellaneous olefins such vinyl ketones, acrylonitrile, and acrylates. aryl rings bearing electronically diverse substituents tolerated the conditions to provide ortho‐alkenylation products in high regioselectivities admissible yields.

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
Base-mediated formal [4+1] annulation of ortho-hydroxyphenyl substituted para-quinone methides and CF3-imidoyl sulfoxonium ylides to access trifluoroacetimidoyl-substituted 2,3-dihydrobenzofurans DOI
Chen Li,

Mingshuo Zhou,

Zhengkai Chen

et al.

Journal of Fluorine Chemistry, Journal Year: 2024, Volume and Issue: 277, P. 110308 - 110308

Published: June 7, 2024

Language: Английский

Citations

1
Site Specific C3‐Alkenylation of Indoles Mediated by in situ C‐H Iodination DOI
Yongli Zhao,

Dingsheng Cao,

Jie‐Ping Wan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract The C3‐alkenylation of indoles have been developed by means a novel in situ iodination tactic which is capable mediating the Heck coupling with alkenes. method features specific site‐selectivity oriented C−I bond, high‐step efficiency without pre‐functionalization for C‐halogen bond construction, as well highly general tolerance to different terminal alkenes, including unactivated acrylates, acrylic acid, vinyl sulfone functionalized natural products.

Language: Английский

Citations

0
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

Citations

0