Recent Progress on Organic Electron Donors (OEDs) Enabled Radical Reactions DOI Open Access
Yu Shao, Xiaodong Jia

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

Published: Oct. 21, 2024

Abstract Over the past few decades, organic transformations facilitated by small molecules have witnessed considerable advancements. Small been widely applied to construction of various skeletons. However, reduction as one fundamental reactions is generally initiated metal‐containing reducing agents, although initial progress electron donors (OEDs) enabled reductive cleavage some chemical bonds had achieved in 1990s. Due their structural diversity and tunability, OEDs can overcome limitations metal‐based such low selectivity poor functional group tolerance well environmental problems caused substantial inorganic waste after reactions. Building on a brief historical overview OED research, this review focuses rencent advancements promoted radical It covers C−X (X=C, O, N etc.) single bonds, cyclization, intermolecular addition unsaturated coupling, functionalization aromatics, C−H bond activation. Additionally, mechanistic insights typical are highlighted for understanding reaction mode involving OEDs.

Language: Английский

Copper-Catalyzed Domino Three-Component Benzannulation: Access to Isoquinolines DOI
Peng Ma, Yuhang Wang, Jianhui Wang

et al.

Organometallics, Journal Year: 2022, Volume and Issue: 41(16), P. 2235 - 2239

Published: Aug. 4, 2022

We report herein the synthesis of isoquinolines through a copper(I)-catalyzed domino reaction. During this transformation, three molecules terminal alkynes, 2-bromoaryl aldehydes (ketones), and acetamide react together, in sequence including Sonogashira coupling, condensation, 6-endo-dig cyclization, elimination acetic acid, hydrolysis. In reaction, with broad functional group tolerance were successfully obtained by using as nitrogen source, which provides an alternative to odorous toxic amines.

Language: Английский

Citations

9
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
Organic Bases as the Organic Electron Donors (OED) Promoted Reductive Coupling of Diarylhalomethanes: Halogens Controlled Construction of Tetraarylethylenes and Tetraarylethanes DOI

Tong Li,

Jie Mao, Shuwei Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13101 - 13109

Published: Sept. 2, 2024

Using the organic base as electron donors, reductive coupling of diaryhalomethanes was smoothly achieved under transition-metal-free reaction conditions, giving a series synthetically important tetraarylethylenes and tetraarylethanes in high yields. The mechanistic study revealed that bases acting donor initiated generation radical intermediate, realizing construction tetraarylethylene tetraarylethane skeletons.

Language: Английский

Citations

1
Synthesis of Indole- and Benzofuran-Based Benzylic Sulfones by Palladium-Catalyzed Sulfonylation of ortho-Iodoaryl Allenes DOI
Yuan Yin,

Cangzhu Hu,

Jing Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16653 - 16662

Published: Nov. 6, 2024

A highly efficient palladium-catalyzed domino coupling reaction of

Language: Английский

Citations

1
Synthesis of Tryptamines from Radical Cyclization of 2-Iodoaryl Allenyl Amines and Coupling with 2-Azallyls DOI
Bo Wang, Minyan Li, Gui Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 8099 - 8103

Published: June 8, 2022

An efficient synthesis of tryptamines is developed. Indole structures were constructed using 2-iodoaryl allenyl amines as electron acceptors and radical cyclization precursors. Radical–radical coupling indolyl methyl radicals azaallyl led to the tryptamine derivatives. The utility versatility this method are showcased by 22 examples in ≤88% yield. In each case, indole formation accompanied situ removal Boc protecting group.

Language: Английский

Citations

7
Regiodivergent cascade cyclization/alkoxylation of allenamides via N-protecting group driven rearrangement to access indole and indoline derivatives DOI

Dhananjay Chaudhary,

Suman Yadav, Naveen Kumar Maurya

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(80), P. 11300 - 11303

Published: Jan. 1, 2022

A mild, palladium-catalyzed domino Heck-cyclization/alkoxylation sequence of aryl halide tethered allenamides is described, providing regiodivergent indole and indoline derivatives controlled by the N-protecting group. This room temperature reaction provided a functionalizable olefinic moiety with broad substrate scope. Preliminary mechanistic studies support rearrangement an indoline-derived intermediate to indoles N-acetyl forming free (NH) indoles.

Language: Английский

Citations

7
Ruthenium(II)-Catalyzed Annulation of Oximes with Maleimides: Synthesis of Pyrrolo[3,4-c]isoquinoline-1,3-diones DOI
Ebrahim Kianmehr, Maryam Shafiee-Pour

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 6977 - 6982

Published: Aug. 5, 2024

A series of pyrroloisoquinoline-1,3-diones has been synthesized using ruthenium(II) as the catalyst and oxygen oxidant in a straightforward manner. The reaction proceeds through tandem C-C/C-N bond formation process between maleimides ketoximes, providing direct approach for synthesis titled products. This operationally simple procedure supplies suitable conditions synthesizing diverse isoquinoline-based heterocycles with range functional groups moderate to good yields compatible gram-scale synthesis. Furthermore, compatibility this green environmentally friendly raises importance present method.

Language: Английский

Citations

1
Visible-light-driven Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals to Access β-Amido Ketone Derivatives DOI Creative Commons
Yonggang Jiang, Hui Li,

H. Tang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 3, 2024

Hydrogen atom transfer (HAT) processes provide an important strategy for selective C-H functionalization. Compared with the popularity of 1,5-HAT processes, however, net-1,2-HAT reactions have been reported less frequently. Herein, we report a unique visible-light-mediated amidyl radicals synthesis β-amido ketone derivatives. Single-electron (SET) to

Language: Английский

Citations

0
Rhodium(III)‐Catalyzed [4+2] Annulation of N‐Hydroxyoximes with Maleate Esters/2‐Chloroacrylates: Synthesis of Isoquinoline‐3,4‐Dicarboxylates and Isoquinoline‐3‐Carboxylates DOI Open Access
He Li, Tao Chen,

Zhiwei Wang

et al.

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

Published: Dec. 27, 2024

Abstract A novel Rh(III)‐catalyzed [4+2] annulation of N ‐hydroxyoximes with maleate esters/2‐chloroacrylates is disclosed, in which diverse isoquinoline skeleton compounds were generated moderate to excellent yields. The protocol exhibits a good compatibility functional groups and wide scope substrates without using any external metal oxidants. Gram‐scale derivatization reactions performed show the potential utility this transformation.

Language: Английский

Citations

0
Catalytic Chemo‐ and Regioselective Radical Carbocyanation of 2‐Azadienes for the Synthesis of α‐Amino Nitriles DOI

Shengzu Duan,

Ya Du, Lingling Wang

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(19)

Published: March 10, 2023

Abstract α‐Amino nitriles are versatile structural motifs in a variety of biologically active compounds and pharmaceuticals they serve as valuable building blocks synthesis. The preparation α‐ β‐functionalized α‐amino from readily available scaffolds, however, remains challenging. Herein is reported novel dual catalytic photoredox/copper‐catalyzed chemo‐ regioselective radical carbocyanation 2‐azadienes to access functionalized by using redox‐active esters (RAEs) trimethylsilyl cyanide. This cascade process employs broad scope RAEs provides the corresponding nitrile 50–95 % yields (51 examples, regioselectivity >95 : 5). products were transformed into prized acids. Mechanistic studies suggest coupling process.

Language: Английский

Citations

1