Photoredox/Nickel Dual-Catalysis-Enabled Regioselective Cyclization of Alkenes with Alkyl Chlorides DOI

Xuege Yang,

Lou Shi, Ruoyu Qin

et al.

Published: Jan. 1, 2023

A photoredox/nickel dual catalysis is presented for the construction of several kinds useful nitrogen-containing heterocycles. This protocol regioselective and features a broad substrate scope. It provides direct access to heterocycles by reacting alkyl chlorides with readily available activated unactivated alkenes. Moreover, this can be easily scalable gram-scale, it feasible use sunlight as light source. Mechanistic studies suggest that energy transfer pathway involved in catalytic process.

Language: Английский

Photoredox/nickel dual-catalysis-enabled synthesis of N-heterocycles from alkyl chlorides and alkenes DOI

Xuege Yang,

Lou Shi, Ruoyu Qin

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 553, P. 113806 - 113806

Published: Jan. 1, 2024

Language: Английский

Citations

6

Bifunctional two-carbon reagent made from acetylene via 1,2-difunctionalization and its applications DOI
Bo Yang,

Kangkui Li,

Yongdong Wang

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(3), P. 936 - 944

Published: Jan. 8, 2024

Language: Английский

Citations

5

Cobalt-Catalyzed Chemoselective and Divergent Synthesis of Vinylsilanes through Hydrosilylation of Acetylene DOI

Xianyang Long,

Dong Zhu, Shifa Zhu

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4429 - 4440

Published: Feb. 28, 2025

Language: Английский

Citations

0

1,2-Dichloroethane as a Gaseous Acetylene Source for the Rapid Assembly of Isoquinolino[1,2-b]quinazolinone Scaffolds DOI
Xinxin Zhu, Mengyao Shi,

Cuilian Xu

et al.

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

Published: April 9, 2025

Reported herein is a novel ruthenium(II)-catalyzed [4 + 2] annulation of quinazolinones with 1,2-dichloroethane (DCE), resulting in myriad isoquinolino[1,2-b]quinazolinone scaffolds. In this protocol, DCE serves not only as solvent but also an acetylene source. The fused undergo versatile transformations and provide rapid convenient way to access several important bioactive molecule analogues such Rutecarpine, Euxylophoricine B E. potential reaction pathway was elucidated through detailed mechanistic studies Density Functional Theory (DFT) calculations.

Language: Английский

Citations

0

Recent progress in the catalytic transformation of acetylene DOI
Xin Yu, Shifa Zhu

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Acetylene, a traditional industrial raw material, has garnered increasing attention in modern organic synthesis over the past two decades.

Language: Английский

Citations

0

Photoinduced synthesis of C2-linked phosphine oxides via radical difunctionalization of acetylene DOI

Kangkui Li,

Jiazhen Deng,

Xianyang Long

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(18), P. 7253 - 7258

Published: Jan. 1, 2023

A photocatalyzed radical difunctionalization of acetylene was achieved, which enables the green synthesis C2-linked phosphine oxides.

Language: Английский

Citations

9

Nickel-Catalyzed Reductive Allylation of Aldehydes with Allylic Alcohols in the Presence of CO2 DOI
Zeyu Zhang, Jiayuan Li, Chanjuan Xi

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8178 - 8182

Published: Nov. 7, 2023

CO2-assisted and Ni-catalyzed direct reductive allylation of aldehydes utilizing allylic alcohols as precursor has been reported. Various homoallyl could be synthesized in excellent yield with enhanced regioselectivity stereoselectivity for alkyl- aryl-substituted under mild conditions. For different substrates, proper collocation the catalytic ligand is crucial. Preliminary mechanistic studies supported reaction pathway through a sequential allyl hydrocarbonate formation/allylnickelation/coordination insertion process by Ni(I)/Ni(III) cycle, which proven cyclic voltammetry analysis.

Language: Английский

Citations

8

Ligand Control of Copper-Mediated Cycloadditions of Acetylene to Azides: Chemo- and Regio-Selective Formation of Deutero- and Iodo-Substituted 1,2,3-Triazoles DOI
Dongying Li,

Shanguang Qiu,

Yunlong Wei

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(2), P. 825 - 834

Published: Dec. 28, 2023

The participation of σ-monocopper and σ-bis-copper acetylide in mechanistic pathways for copper-catalyzed cycloaddition (CuAAC) reactions acetylene with azides was probed by analysis deuterium distributions the 1,2,3-triazole product formed deuterolysis initially mono- bis-copper triazoles. results show that, when Cu(Phen)(PPh3)2NO3 is used as catalyst DMF/D2O, 1-substituted-5-deutero-1,2,3-triazoles are generated selectively. This finding demonstrates that Cu(Phen)(PPh3)2NO3-catalyzed cycloadditions utilize monocopper substrate produce 5-copper-1,2,3-triazoles initially. Conversely, DBU or Et3N copper ligand, process takes place through initial formation to 4,5-bis-copper-triazole, which reacts D2O form corresponding 4,5-bis-deutero-triazole. Moreover, C2D2 substrate, Cu H2O/DMF solvent, mono-C4-deutreo 1,2,3-triazoles high yields excellent levels regioselectivity. Lastly, CuAAC azides, promoted CuCl2·2H2O NaI, yield 4,5-diiodo-1,2,3-triazoles moderate efficiencies.

Language: Английский

Citations

7

Radical Allylation of Aldehydes with Allenes by Photoredox Cobalt and Chromium Dual Catalysis DOI
Lei Shi, Haoyu Li, Xin Wang

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(16), P. 2558 - 2564

Published: May 23, 2024

Abstract A dual cobalt and chromium photoredox-catalyzed allylation of aldehydes with allenes through a photo metal-hydride atom transfer (MHAT) process has been developed to yield homoallylic alcohols exceptional diastereoselective control. This sustainable efficient method holds significant promise for applications in the synthesis valuable organic compounds.

Language: Английский

Citations

2

Modular and Diverse Synthesis of Acrylamides by Palladium‐Catalyzed Hydroaminocarbonylation of Acetylene DOI Creative Commons
Matthias Beller,

Zhusong Cao,

Qiang Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: July 10, 2024

The development of all kinds covalent drugs had a major impact on the improvement human health system. Covalent binding to target proteins is achieved by so-called electrophilic warheads, which are incorporated in respective drug molecule. In last decade, specifically acrylamides emerged as attractive warheads design. Herein, straightforward palladium-catalyzed hydroaminocarbonylation acetylene has been developed, allowing modular and diverse synthesis bio-active acrylamides. This general protocol features high atom efficiency, wide functional group compatibility, chemoselectivity proceeds additive free under mild reaction conditions. synthetic utility this showcased ibrutinib, osimertinib, other compound derivatives.

Language: Английский

Citations

2