Copper-Catalyzed Diboron-Mediated cis-Semi-Hydrogenation of Alkynes under Facile Conditions DOI Creative Commons

Yuxi Zeng,

Honggang Zhang,

Daofan Ma

et al.

Molecules, Journal Year: 2022, Volume and Issue: 27(21), P. 7213 - 7213

Published: Oct. 25, 2022

Cis-alkenes are ubiquitous in biological molecules, which makes it greatly significant to develop efficient methods toward construction of cis-olefins. Herein, we reported a facile semi-hydrogenation alkynes cis-alkenes an way with cuprous bromide/tributylphosphine as the catalyst and bis(pinacolato)diboron/methanol hydrogen donor. The method features convenient reaction conditions, wide substrate scope, high yields, stereoselectivity.

Language: Английский

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures DOI
Han Liu, Lei Wang, Jin‐Tao Yu

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

Citations

23

Photocatalytic Cyclization Cascades by Radical Relay toward Pyrrolo[1,2-a]indoles: Synthesis, Mechanism, and Application DOI

Chen He,

Qi Wang,

Xiaoyang Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3509 - 3524

Published: Feb. 16, 2024

A photocatalytic annulation cascade of unactivated N-alkene-linked indoles with Langlois' reagent by a radical relay is developed at room temperature under blue LED irradiation. The reaction afforded series tri/difluoromethylated pyrrolo[1,2-a]indoles in moderate to good yields. DFT study suggests that the ascribed rhodamine 6G-induced cyclization involving vinyl addition-radical and hydrogen-atom-abstraction (HAA) processes, interestingly, are applied as fluorescent dyes into fluorescence spectrum live-cell imaging. This paper represents an initial example on cascades HAA process.

Language: Английский

Citations

9

A Deeper Understanding of H2 Evolution Entirely from Water via Diborane Hydrolysis DOI
Xiang Liu, Xinyu Zhang, Gaixia Zhang

et al.

ACS Materials Letters, Journal Year: 2023, Volume and Issue: 5(3), P. 783 - 797

Published: Feb. 6, 2023

Hydrogen (H2) has drawn extensive attention due to its superior gravimetric capacity density and eco-friendly nature. Nowadays, hydrogen is mainly produced by the steam reforming of natural gas, a process that leads massive emissions greenhouse gases. Very recently, H2 evolution upon hydrolysis diboranes (e.g., B2(OH)4 B2pin2) promising because both H atoms released are obtained from water. This different sodium borohydride, dimethylaminoborane, ammonia borane, tetramethyldisiloxane, where an generated with only one atom H2O other storage materials. Importantly, diborane in D2O could provide easy simple method for D2 evolution. In this minireview, overview extraordinary emphasis on recent developments mechanism study applications presented. The future research perspectives have been suggested commercialization as well.

Language: Английский

Citations

14

Iron-Mediated Hydrogen Atom Transfer Radical Cyclization of Alkenyl Indoles and Pyrroles Gives Their Fused Derivatives: Total Synthesis of Bruceolline E and H DOI
Santosh J. Gharpure, Rupali S. Chavan,

S. Narang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4583 - 4588

Published: Feb. 11, 2024

The iron-mediated hydrogen atom transfer (HAT) reaction is efficaciously employed for the synthesis of dihydropyrroloindoles and dihydropyrrolizines via 5-exo-trig radical cyclization where indoles pyrroles are used as an acceptor. This approach has also been extended tetrahydrocyclopenta[b]indolones Baldwin-disfavored 5-endo-trig pathway. formal bruceolline J total bruceollines E H have expeditiously carried out by employing former strategy.

Language: Английский

Citations

6

Metal-free polychloromethyl radical-initiated cyclization of unactivated N-allylindoles towards pyrrolo[1,2-a]indoles DOI

Yujia Shan,

Zixian Yang,

Jin‐Tao Yu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(26), P. 5259 - 5263

Published: Jan. 1, 2022

A polychloromethylation-initiated cyclization of N -allyl-indoles towards pyrrolo[1,2- a ]indoles was developed using CH 2 Cl and CHCl 3 as the di- trichloromethyl radical sources.

Language: Английский

Citations

18

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H2 Generation DOI Creative Commons
Qiuxia Zhao, Xiang Liu, Didier Astruc

et al.

European Journal of Inorganic Chemistry, Journal Year: 2023, Volume and Issue: 26(11)

Published: Feb. 24, 2023

Abstract Diboron compounds with a B−B bond, discovered B 2 Cl 4 century ago, have been developed only since the turn of this for catalyzed borylation reactions, mostly well‐know reagent bis(binacolato)diboron, (B pin ). On other hand, chemistry tetrahydroxydiboron (THDB), also named bis‐boric acid, is relatively underdeveloped. In review, properties THDB as borylation, reductant (including transfer hydrogenation), catalyst, source radicals and generator H from water upon hydrolysis are summarized.

Language: Английский

Citations

10

Radical Cascade Cyclization of Unactivated Alkene-Tethered Indoles with Aryldiazonium Salt and Sodium Metabisulfite to Access Azo- and Sulfonylated-2,3-Dihyro-1H-pyrrolo[1,2-a]indoles DOI
Pawan Kumar, Archana Rai, Manish Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 9123 - 9129

Published: June 28, 2023

A method for the construction of heterocyclic scaffold 2,3-dihyro-1H-pyrrolo[1,2-a]indoles via arylsulfonyl radical-triggered cascade cyclization unactivated alkene-tethered indoles in absence any external photocatalyst has been developed. This protocol features easily accessible starting materials such as sodium metabisulfite and aryldiazonium tetrafluoroborates at room temperature offers good functional group compatibility, enabling introduction various functionalized sulfonyl azo groups into pyrrolo[1,2-a]indoles.

Language: Английский

Citations

9

Metal-free polychloromethylation/cyclization of unactivated alkenes towards ring-fused tricyclic indolones and benzoimidazoles DOI

Yechun Wu,

Han Liu,

Lingli Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(35), P. 7079 - 7084

Published: Jan. 1, 2023

Polychloromethylative cyclization of N-alkenyl indoles was developed under metal-free conditions to afford tricyclic pyridoindolones and pyrroloindolones in moderate good yields. In the reaction, commercially available CHCl3 CH2Cl2 were employed as tri- dichloromethyl radical sources. Moreover, dichloromethylated polycyclic benzoimidazoles can also be obtained standard conditions.

Language: Английский

Citations

9

Visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF3 for the synthesis of trifluoromethylated pyrrolo[1,2–a]indoles DOI

Hongni Qin,

Yong Zhang, Song Sun

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155468 - 155468

Published: Jan. 1, 2025

Language: Английский

Citations

0

Nickel-Catalyzed and Tetrahydroxydiboron-Mediated Allylation of Aldehydes with Allyl Alcohols DOI
Yingfan Yang,

Siyi Zhong,

Daofan Ma

et al.

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

Published: Feb. 3, 2025

The allylation of carbonyl compounds to form homoallylic alcohols represents one the significant synthetic transformations. In this letter, we describe a new method for aldehydes with allyl facilitated by nickel chloride and tetrahydroxydiboron. This approach offers mild straightforward procedure synthesis from ketones.

Language: Английский

Citations

0