Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones DOI

Jing‐Tong Deng,

Ming Lang, Jin‐Bao Peng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4644 - 4648

Published: Aug. 20, 2024

Abstract The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most these reactions proceed via carbometalation‐initiated 5‐ exo ‐trig followed by nucleophilic trapping the resulting σ alkyl‐metal species achieve diverse functionalized oxindoles. 6‐ endo type been rarely reported. Herein, zinc‐mediated amination alkylidenecyclopropane‐tethered chlorides with anilines for synthesis 2‐quinolones was developed. A range different substituted were prepared in 65–89% yield from and aniline derivatives using Zn/TMSCl system.

Language: Английский

Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines DOI
Ao-Long Li,

R.-Q. Xie,

Quan Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A photochemical radical cascade cyclization reaction of isocyanides with α-carbonyl bromides under mild conditions is disclosed for accessing 1,4-dibenzodiazepines, demonstrating good tolerance towards various functional groups.

Language: Английский

Citations

0
Theoretical studies on the mechanism of Rh-catalyzed [(3+2+2)] cycloisomerization reactions of dienophile-substituted alkylidenecyclopropanes DOI
Wanjun Zhao,

XU Hui-min,

Ying Ren

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 579, P. 115055 - 115055

Published: March 29, 2025

Language: Английский

Citations

0
Metal-Free Visible-Light Excitation of TMSN3 Enables [3 + 2] Cycloaddition of Arylidenecyclopropanes with Olefins DOI
Yayu Wang,

Ting-Feng Fu,

Xiao Hu

et al.

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

Published: April 14, 2025

A visible-light photoredox [3 + 2] cycloaddition reaction of arylidenecyclopropanes with olefins was developed, employing the readily available and commercially accessible TMSN3 as an efficient radical mediator. This method provides a convenient route to arylidenecyclopentanes from starting materials, is metal-free, features enhanced atom step economy, excellent selectivity, extensive substrate versatility, favorable functional group compatibility, structural diversity, mild conditions, which further enable late-stage diversification. DFT calculations elucidated that this transformation entails sequential generation, addition, ring-opening, cyclization, elimination steps.

Language: Английский

Citations

0
Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines DOI

Qin Luo,

Z.‐F. XIE,

Cen Jian

et al.

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

Published: May 19, 2025

Herein, we present a protocol for the construction of functionalized quinolines, i.e., 3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines (ATFQLs) 4, from ortho-vinyl enaminones and 1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one, which was catalyzed by FeCp2 promoted FeCl3 (Lewis acid) additives in solvents (i.e., acetonitrile toluene). This strategy first utilized FeCp2-catalyzed functionalization alkenes with trifluoromethyl radicals. The intermediate formed captured ortho-iodobenzoate substrate, yielding 3, then underwent FeCl3-catalyzed elimination at higher temperature to form an α,β-unsaturated intermediate. subsequent intramolecular Michael reaction yielded final target compound 4. In summary, series ATFQLs 4 were synthesized through formation two bonds (C═C C-C).

Language: Английский

Citations

0
Chelation-Controlled Stereospecific Ring-Opening Arylation of α-Aminoaryl-Tethered Alkylidenecyclopropanes: Stereoselective Synthesis of Polysubstituted Conjugated Dienes DOI

Miao-Miao Ji,

Ying Tang, W. LUO

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A palladium-catalyzed stereospecific ring-opening arylation of α-aminoaryl-tethered alkylidenecyclopropanes for the stereoselective synthesis 1,1,2-trisubstituted conjugated dienes has been developed.

Language: Английский

Citations

0
Manganese-Catalyzed Cycloalkene Ring Expansion Synthesis of Azaheterocycles DOI Creative Commons
Zhixin Wang, Hanxiao Xu,

Xuanzhen Han

et al.

Published: June 18, 2024

Radical chemistry is synthetically useful but can be plagued by the non-intuitive reaction course and indiscriminate reactivity profile. Herein, dynamic radical effect revealed as a conceptual logic for predictive achievement of selectivity. The reversible bonding association/dissociation two radicals serves synthetic handle directing one to target recourse, without participation other radical. A Mn catalytic protocol has been developed cycloalkene ring expansion synthesis azaheterocycles. An initial azidyl addition alkene subsequent O2 occupation C-radical site prevents further coupling steers toward intramolecular rearrangement pathway. broad substrate scope established pyridine isoquinoline derivatives. This new perspective promises an important guiding principle empowering radical-based chemical transformations.

Language: Английский

Citations

2
Manganese-Catalyzed Cycloalkene Ring Expansion Synthesis of Azaheterocycles DOI
Zhixin Wang, Hanxiao Xu,

Xuanzhen Han

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 2, 2024

Herein, a Mn catalytic protocol has been developed for the cycloalkene ring expansion synthesis of azaheterocycles, allowing broad-substrate-scope access to pyridine and isoquinoline derivatives. The initial monoaddition an azidyl radical alkene further as-generated C-radical addition O

Language: Английский

Citations

1
Low-Valent Tungsten Catalyzed Carbonylative Synthesis of Benzoates from Aryl Iodides and Alcohols DOI Creative Commons
Feihua Ye, Lu Lin, Zhaoyang Huang

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(22), P. 5305 - 5305

Published: Nov. 10, 2024

Non-noble metals catalyzed carbonylative reactions serve as straightforward and sustainable methods for the synthesis of functionalized carbonyl-containing compounds. Herein, a low-valent-tungsten-catalyzed reaction that enables coupling aryl iodides alcohols or phenols was disclosed, employing readily available W(CO)

Language: Английский

Citations

1
Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones DOI

Jing‐Tong Deng,

Ming Lang, Jin‐Bao Peng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4644 - 4648

Published: Aug. 20, 2024

Abstract The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most these reactions proceed via carbometalation‐initiated 5‐ exo ‐trig followed by nucleophilic trapping the resulting σ alkyl‐metal species achieve diverse functionalized oxindoles. 6‐ endo type been rarely reported. Herein, zinc‐mediated amination alkylidenecyclopropane‐tethered chlorides with anilines for synthesis 2‐quinolones was developed. A range different substituted were prepared in 65–89% yield from and aniline derivatives using Zn/TMSCl system.

Language: Английский

Citations

0