Visible‐Light‐Induced Denitroalkylation of β‐Nitrostyrenes with Alkyl Boronic Acids DOI

Mingli Xu,

Chenyue Zhao,

Yongxiang Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 22, 2023

Abstract Without an additional activator, the visible‐light‐catalyzed denitroalkylation of β ‐nitrostyrenes and alkyl boronic acids is reported. The efficient coupling cyclic secondary with various aryl nitroolefins realized, which gives olefins in 47–87 % yields. A possible mechanism involving fact that nitrite released from ‐nitrostyrene upon irradiation further activates to generate radicals proposed based on control experiments a literature survey.

Language: Английский

Copper-Catalyzed 1,4-Alkylarylation of 1,3-Enynes with Ethers and Aryl Boronic Acids Enabled via C(sp3)–H Functionalization DOI
Yunhe Lv,

Weiya Pu,

Le Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1478 - 1488

Published: Jan. 17, 2025

Herein, we present a copper-catalyzed, three-component intermolecular 1,4-alkylarylation of 1,3-enynes with ethers and aryl boronic acids. This method, driven by α-C(sp3)-H functionalization the oxygen atom in ethers, regioselectively produces various tetrasubstituted allenes from simple, readily available precursors. Key features include mild reaction conditions simple catalytic system.

Language: Английский

Citations

0
Cp2Fe-Mediated Electrochemical Synthesis of Phosphorylated Oxindoles and Indolo[2,1-a]isoquinolin-6(5H)-ones DOI

Xiaocong Zhou,

Jian Wang, Yirui Shen

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 17521 - 17526

Published: Nov. 22, 2023

An efficient and environmentally friendly electrochemical synthesis of phosphorylated oxindoles indolo[2,1-a]isoquinolin-6(5H)-ones mediated by readily available Cp2Fe has been developed, which illustrated a broad substrate scope diverse functional group compatibility. This protocol featured an external oxidant-free process was at room temperature, proposed to be driven the anodic oxidation Cp2Fe.

Language: Английский

Citations

9
Formation of cyclopenta[c]quinolines through visible-light-induced photoredox cascade bis-annulations of 1,7-enynes with sulfoxonium ylides DOI

Ning Xian,

Guo‐Jun Deng, Huawen Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(37), P. 7618 - 7622

Published: Jan. 1, 2024

A novel visible-light-driven photoredox-catalyzed cascade bicyclization of 1,7-enynes with aqueous sulfoxonium ylides is reported. The reaction highly chemoselective three new C-C bonds, two rings, and an all-carbon quaternary stereocenter constructed in a one-pot fashion. This mild protocol features remarkably broad substrate scope good functional group tolerance, providing general practical approach to access various cyclopenta[

Language: Английский

Citations

2
Synthesis of Acyl Cyclopentaquinolinones through Simultaneous Construction of the Heterocyclic Scaffold and Introduction of the Acyl Group DOI

Lian Xue,

Chang Gao, Xinying Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6292 - 6305

Published: April 16, 2024

Presented herein is an effective and concise synthesis of acyl cyclopentaquinolinone derivatives via the cascade reactions N-(o-ethynylaryl)acrylamides with α-diazo carbonyl compounds. The formation product involves a visible light-induced radical from compound followed by its addition onto acrylamide moiety to trigger double annulation, single-electron oxidation, β-elimination. To our knowledge, this first example in which scaffold was constructed along introduction group under light irradiation conditions. Compared literature methods for similar purpose, newly developed protocol has advantages such as readily accessible substrates, mild reaction conditions, valuable products, synthetic procedure, high sustainability. With all these merits, method expected find wide applications construction related heterocyclic skeletons.

Language: Английский

Citations

1
Photoinduced Alkenylation of Alkenyl Sulfones with EDA Complexes between NHPI Esters and HE DOI

Mingli Xu,

Chenyue Zhao,

Yongxiang Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(7)

Published: April 17, 2024

Abstract A novel alkenylation reaction between N ‐hydroxyphthalimide (NHPI) esters and alkenyl sulfones is reported. It undergoes the formation of electron donor‐acceptor (EDA) complex a series alkenes are obtained in good to excellent yields. has advantages simple operation, mild conditions, metal‐free.

Language: Английский

Citations

1
Ruthenium and Iodine Anion Cocatalyzed Cascade Dihalogenation and Cyclization of Internal Alkyne-Tethered Cyclohexadienones with 1,2-Dihaloethanes DOI
Xiaoli Huang, Yi Cui,

Meiqi Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9686 - 9694

Published: June 22, 2024

We have established an efficient ruthenium(II) and iodine anion cocatalyzed dihalogenation cascade cyclization of internal alkyne-tethered cyclohexadienones, which stereoselectively afforded numerous products with a bioactive hydrobenzofuran skeleton in high yields under mild conditions. In this transformation, the reaction pathway was determined by concentration electrophilic reagent, also provided strategy for control selectivity. Furthermore, method features use 1,2-dihaloroethane as halogen source via catalyst.

Language: Английский

Citations

1
Oxidation of C–H Bond Adjacent to Oxygen of Ethers DOI
Le Liu, Pin Gao, Xin Hong

et al.

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

Citations

0
Radical Cascade Reaction of Heterocyclic Ketene Aminals with Thiocyanates Promoted by Visible Light: Synthesis of Functionalized Fused 2-Iminothiazolines DOI

Shu Shu Yang,

Tingting Guo, Jianbo Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13678 - 13690

Published: Sept. 6, 2024

Herein, a visible-light-promoted radical cascade cyclization of heterocyclic ketene aminals (HKAs) and thiocyanates was developed to access functionalized fused 2-iminothiazolines. This novel reaction can be realized under only visible-light irradiation without the help external photocatalysts, oxidants, additives. These multicomponent reactions demonstrate excellent selectivity for

Language: Английский

Citations

0
Cu/Pd-Catalyzed Domino Carbonylative Synthesis of Polycyclic Carbonyl-Containing Quinolin-2(1H)-one Scaffolds from α-Bromocarbonyls DOI

Jianwei Wang,

Shangyuan Wang,

Shuwei Li

et al.

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

Published: Nov. 22, 2024

A novel Cu/Pd-catalyzed domino radical cyclization and C-H carbonylation of α-bromocarbonyls has been developed, which enables the rapid incorporation CO unit into polycyclic quinolin-2(1

Language: Английский

Citations

0
Visible‐Light‐Induced Denitroalkylation of β‐Nitrostyrenes with Alkyl Boronic Acids DOI

Mingli Xu,

Chenyue Zhao,

Yongxiang Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 22, 2023

Abstract Without an additional activator, the visible‐light‐catalyzed denitroalkylation of β ‐nitrostyrenes and alkyl boronic acids is reported. The efficient coupling cyclic secondary with various aryl nitroolefins realized, which gives olefins in 47–87 % yields. A possible mechanism involving fact that nitrite released from ‐nitrostyrene upon irradiation further activates to generate radicals proposed based on control experiments a literature survey.

Language: Английский

Citations

1