Water-Involved 1,3-Aminoxylation of Fluoroalkenes: Chemo-, Regio-, and Stereoselective Synthesis of β-Fluoroacyl Vinylamines DOI
Chi Zhang, Xueying Huang,

Shu-Ji Gao

et al.

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

Published: April 9, 2025

Perfluoroalkyl alkenyl iodides (PFAIs) are emerging as highly reactive, storage-stable, and multifunctional fluoroalkyl-bearing reagents, facilitating the manufacture of value-added organofluorides through multi-halo-functionalization. Herein, we developed a water-involved 1,3-aminoxylation PFAIs with sulfonamides for chemo-, regio-, Z-stereoselective synthesis valuable β-fluoroacyl vinylamines. This reaction proceeded via sequential deiodoamination defluoroxylation process under transition-metal-free conditions, featuring broad substrate scope good functional group tolerance. Compared to reported methods, some drawbacks, such multistep manipulation, harsh need expensive catalysts, use toxic/sensitive could be eliminated. Furthermore, synthetic potential this method was demonstrated scale-up synthesis, postfunctionalization complex molecules, ready transformation products.

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
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
Organic Base-Catalyzed Cascade Reaction of CF3–Iminopropargylic Alcohols with Carboxylic Acids: an Approach to β-CF3 β-Aminoenones DOI
Ruslan S. Shulgin,

O. G. Volostnykh,

А. В. Степанов

et al.

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

Published: Feb. 6, 2025

A novel approach to the synthesis of β-CF3 β-aminoenones by organic amine base-catalyzed reaction CF3-iminopropargylic alcohols with carboxylic acids is reported. The advantages protocol are ease operation, available starting materials, and simple tertiary catalysts.

Language: Английский

Citations

0
Synthesis of Spiro 3,3′-Cyclopropyl Oxindoles via Cyclopropanation of 3-Alkenyl-oxindoles with CF3-Imidoyl Sulfoxonium Ylides DOI
Chen Li, Yu Zhang, Zhengkai Chen

et al.

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

Published: March 4, 2025

A catalyst and additive-free [2+1] annulation of 3-alkenyl-oxindoles with CF3-imidoyl sulfoxonium ylides (TFISYs) for the construction spiro 3,3'-cyclopropyl oxindoles has been achieved. cascade intermolecular Micheal-addition reaction intramolecular nucleophilic substitution sequence might be involved in transformation, which afforded a wide range multisubstituted oxindole products high efficiency diastereoselectivity.

Language: Английский

Citations

0
Water-Involved 1,3-Aminoxylation of Fluoroalkenes: Chemo-, Regio-, and Stereoselective Synthesis of β-Fluoroacyl Vinylamines DOI
Chi Zhang, Xueying Huang,

Shu-Ji Gao

et al.

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

Published: April 9, 2025

Perfluoroalkyl alkenyl iodides (PFAIs) are emerging as highly reactive, storage-stable, and multifunctional fluoroalkyl-bearing reagents, facilitating the manufacture of value-added organofluorides through multi-halo-functionalization. Herein, we developed a water-involved 1,3-aminoxylation PFAIs with sulfonamides for chemo-, regio-, Z-stereoselective synthesis valuable β-fluoroacyl vinylamines. This reaction proceeded via sequential deiodoamination defluoroxylation process under transition-metal-free conditions, featuring broad substrate scope good functional group tolerance. Compared to reported methods, some drawbacks, such multistep manipulation, harsh need expensive catalysts, use toxic/sensitive could be eliminated. Furthermore, synthetic potential this method was demonstrated scale-up synthesis, postfunctionalization complex molecules, ready transformation products.

Language: Английский

Citations

0