In situ generated CF3CHN2 with 3-ylideneoxindoles to access CF3-containing pyrazolo[1,5-c]quinazolines derivatives DOI Creative Commons

Mougang Hu,

Haitao Zhou,

Yu-Chen Fang

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(49), P. 36410 - 36415

Published: Jan. 1, 2024

A protocol involving a DBU-promoted [3 + 2] cycloaddition/1,3-H shift/rearrangement/dehydrogenation cascade was developed, giving series of CF 3 -containing pyrazole[1,5- c ]quinazolines in 35–86% yields.

Language: Английский

Visible-Light-Induced Defluorinative α-C(sp3)–H Alkylation for the Synthesis of gem-Difluoroallylated α-Trifluoromethylamines DOI

Bingran Chen,

Qinlin Chen,

Yang Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9124 - 9129

Published: Nov. 17, 2023

Herein, we describe a novel and efficient photoredox catalytic Cα radical addition/defluoroalkylation coupling reaction between α-trifluoromethyl alkenes N-trifluoroethyl hydroxylamine. A series of gem-difluoroallylated α-trifluoromethylamines were synthesized by the addition enabled 1,2-H shift in situ-generated radical. Notably, this protocol is distinguished its mild conditions, easy operation, excellent functional group tolerability.

Language: Английский

Citations

16
Diastereo- and Enantioselective Dearomative Reductive Aryl-Fluoroalkenylation of Indoles by Nickel Catalysis DOI

Xinmiao Huang,

Min Ou,

Lixin Hong

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 6432 - 6439

Published: April 11, 2024

Herein, we disclose a nickel-catalyzed dearomative reductive aryl-fluoroalkenylation of indoles by defluorinative coupling with gem-difluoroalkenes. The catalytic protocol affords facile assembly various monofluoroalkene-containing polycyclic fused indolines bearing two contiguous carbon stereocenters in high diastereo- and enantioselectivities tolerance diverse functional groups.

Language: Английский

Citations

5
Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles DOI
Wang Bi,

Jing-Kun Gao,

Shuo Sun

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3739 - 3743

Published: April 29, 2024

An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of N-(o-bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba)2/SPINOL-based phosphoramidite as the chiral catalyst and HCO2Na hydride source, a series enantioenriched spiro indolines bearing vicinal stereocenters were afforded in moderate to good yields with excellent enantioselectivities. The formal tetrasubstituted alkene β-hydrogens therefore realized by inhibiting β-H elimination.

Language: Английский

Citations

4
Visible-Light-Induced Tandem Nickel-Catalyzed Heck Cyclization/Self-Promoted [2+2] Intermolecular Cycloaddition DOI

Xiaogang Tong,

Linlin Ren,

Yonggong Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Visible-light-induced transition metal (TM) catalysis has emerged as a new paradigm to discover unprecedented transformations. The reported nickel species TM photocatalysts are mainly involved in the homolysis of Ni(II) complex or alkyl halide activation. Herein, we describe that photoexcited could facilitate Heck cyclization by accelerating anti-β-hydride elimination. Meanwhile, tandem visible-light-induced substrate self-promoted intermolecular [2+2] photocycloaddition without assistance additional was discovered.

Language: Английский

Citations

0
Asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes by nickel catalysis DOI

Xinmiao Huang,

Xin Tan, Xu Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 5940 - 5949

Published: Jan. 1, 2023

Herein, we report an asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes enabled by nickel catalysis to access structurally diverse gem -difluorovinyl-containing chiral polycyclic indolines.

Language: Английский

Citations

4
Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes DOI

Man Ren,

Shengjiao Yu,

Xuefeng Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8342 - 8356

Published: May 31, 2024

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features this protocol are easy-to-obtain starting materials, a wide range substrates, functional group tolerance as well high atom economy, thus offering strategy to access variety

Language: Английский

Citations

1
Synthesis of substituted (trifluoromethyl)alkenes: (Trifluoromethyl)alkylidenation of thioketones via CF3-thiiranes DOI
Kohei Fuchibe, Tomoya Matsunobu, Junji Ichikawa

et al.

Journal of Fluorine Chemistry, Journal Year: 2024, Volume and Issue: 275, P. 110273 - 110273

Published: March 23, 2024

Language: Английский

Citations

0
Research Progress in the Synthesis of Azaindoline and Its Derivatives DOI Open Access
Hao Ye,

Haibin Zhang,

Yanan Wu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(4), P. 1106 - 1106

Published: Jan. 1, 2024

The azaindoline skeleton exists in a wide range of bioactive molecules and natural products, has significant biological pharmaceutical activities.The synthesis these compounds attracted great attention from chemists.However, due to the electron-deficient nature pyridine ring where nitrogen atom is located, many traditional methods for indoline cannot effectively construct skeleton.In recent years, chemists have been exploring made some progress.According different reaction types, azaindolines years key mechanisms are reviewed discussed, future development prospect this research field prospected.

Language: Английский

Citations

0
Switchable divergent synthesis of chiral indole derivatives via catalytic asymmetric dearomatization of 2,3-disubstituted indoles DOI Creative Commons
Tingting Liu,

Jianbin Wang,

Rou Xiao

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(22), P. 15591 - 15596

Published: Jan. 1, 2024

A strategy allowing the switchable divergent synthesis of chiral indole derivatives was established via phosphoric acid-catalyzed asymmetric dearomatization 2,3-disubstituted indoles using naphthoquinone monoimines as electrophiles. The products were switched between indolenines and fused indolines according to post-processing conditions. Both two types obtained in good high yields with generally excellent enantioselectivities. NaBH4 found work a promoter well reductant cyclization process leading indolines.

Language: Английский

Citations

0
Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes DOI
Ren‐Xiao Liang,

Chengan Jin,

Yi‐Xia Jia

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(20), P. 3191 - 3198

Published: July 3, 2024

Abstract A silver-catalyzed dearomative decarboxylative [3+2] spiroannulation of aryl oxamic acids with alkynes is described. The reaction provides reliable access to a range azaspiro[4,5]trienones in moderate yields aqueous media. In addition, the exhibits broad substrate scope and good functional group compatibility.

Language: Английский

Citations

0