The C(sp3)–H bond functionalization of thioethers with styrenes with insight into the mechanism DOI
Zhan Yan, Nai‐Xing Wang, Leiyang Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(29), P. 5845 - 5851

Published: Jan. 1, 2022

A metal-free inactive C(sp3)-H bond functionalization of thioethers with styrenes using TBHP as an initiator and DBU a base has been developed. This transformation broken through the low activity realized moderate yields. Herein extended experiments were conducted to confirm radical relay process, reaction energy intermediate transformations.

Language: Английский

Recent advances in organic electrosynthesis employing transition metal complexes as electrocatalysts DOI
Cong Ma, Ping Fang,

Zhao‐Ran Liu

et al.

Science Bulletin, Journal Year: 2021, Volume and Issue: 66(23), P. 2412 - 2429

Published: July 13, 2021

Language: Английский

Citations

293

Electrochemical Late-Stage Functionalization DOI Creative Commons
Yulei Wang, Suman Dana, Hao Long

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(19), P. 11269 - 11335

Published: Sept. 26, 2023

Late-stage functionalization (LSF) constitutes a powerful strategy for the assembly or diversification of novel molecular entities with improved physicochemical biological activities. LSF can thus greatly accelerate development medicinally relevant compounds, crop protecting agents, and functional materials. Electrochemical synthesis has emerged as an environmentally friendly platform transformation organic compounds. Over past decade, electrochemical late-stage (eLSF) gained major momentum, which is summarized herein up to February 2023.

Language: Английский

Citations

141

Electrocatalytic C−N Couplings at Cathode and Anode DOI
Dawei Chen, Jiani Liu,

Jingjun Shen

et al.

Advanced Energy Materials, Journal Year: 2024, Volume and Issue: 14(28)

Published: Feb. 21, 2024

Abstract Electrocatalytic C−N couplings are promising alternatives to construct bonds and synthesize vital chemicals, including amine, amide, amino acid, oxime, imine, nitrile, under ambient conditions. In recent years, the electrocatalytic coupling has attracted a wide range of research interest achieved considerable developments. Here, is systematically reviewed aiming at reductive cathode oxidative anode. cathodic part, reaction systems, corresponding design principles electrocatalysts for different mechanism studies from experimental theoretical aspects, application‐oriented devices summarized. Anodic offers potential approach replace conventional energy‐demand synthesis protocols, an indispensable part green controllable construction unsaturated C = N C≡N bonds. According principle that electron transfer crucial point in anodic coupling, reactions sorted out based on direct indirect paths, respectively. Finally, challenges outlooks this field proposed. appealing topic electrochemistry possesses infinite possibilities future.

Language: Английский

Citations

21

Predicting success in Cu-catalyzed C–N coupling reactions using data science DOI Creative Commons
Mohammad H. Samha, Lucas J. Karas, David B. Vogt

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(3)

Published: Jan. 17, 2024

Data science is assuming a pivotal role in guiding reaction optimization and streamlining experimental workloads the evolving landscape of synthetic chemistry. A discipline-wide goal development workflows that integrate computational chemistry data tools with high-throughput experimentation as it provides experimentalists ability to maximize success expensive campaigns. Here, we report an end-to-end data-driven process effectively predict how structural features coupling partners ligands affect Cu-catalyzed C–N reactions. The established workflow underscores limitations posed by substrates while also providing systematic ligand prediction tool uses probability assess when will be successful. This platform strategically designed confront intrinsic unpredictability frequently encountered deployment.

Language: Английский

Citations

19

Electrooxidative Rhodium‐Catalyzed [5+2] Annulations via C−H/O−H Activations DOI Creative Commons
Yulei Wang, João C. A. Oliveira, Zhipeng Lin

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(12), P. 6419 - 6424

Published: Jan. 20, 2021

Abstract Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of five‐ and six‐membered heterocycles. In contrast, we herein describe first electrochemical [5+2] cycloadditions to assemble valuable seven‐membered benzoxepine skeletons by C−H/O−H activation. The efficient alkyne annulation featured ample substrate scope, using electricity only oxidant. Mechanistic studies provided strong support rhodium(III/I) regime, benzoxepine‐coordinated rhodium(I) sandwich complex catalyst resting state, which was re‐oxidized rhodium(III) anodic oxidation.

Language: Английский

Citations

74

Recent advances in transition metal-catalyzed heteroannulative difunctionalization of alkenes via C–H activation for the synthesis of heterocycles DOI
Jianchao Liu, Xiao Xiao, Yinlong Lai

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(8), P. 2256 - 2279

Published: Jan. 1, 2022

In this review article, we summarized recent advances in the transition metal-catalyzed heteroannulative difunctionalization of alkenes via direct C–H activation to access heterocyclic frameworks.

Language: Английский

Citations

57

Synthesis of P-stereogenic cyclicphosphinic amidesviaelectrochemically enabled cobalt-catalyzed enantioselective C–H annulation DOI
Tao Liu,

Wangqin Zhang,

Chao Xu

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3606 - 3614

Published: Jan. 1, 2023

We describe a cobalta-electro-catalyzed enantioselective C–H annulation of arylphosphinamides with alkynes for P-stereogenic compounds via desymmetrization and kinetic resolution processes.

Language: Английский

Citations

40

Electrochemical methods for synthesis and in situ generation of organometallic compounds DOI
Zufar N. Gafurov, Artyom O. Kantyukov, Alexey A. Kagilev

et al.

Coordination Chemistry Reviews, Journal Year: 2021, Volume and Issue: 442, P. 213986 - 213986

Published: May 13, 2021

Language: Английский

Citations

44

Electrosynthesis of CF3‐Substituted Polycyclic Quinazolinones via Cascade Trifluoromethylation/Cyclization of Unactivated Alkene DOI
Lei Liu,

Wangqin Zhang,

Chao Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(7), P. 1319 - 1325

Published: Feb. 23, 2022

Abstract An atom and step economy cascade trifluoromethylation/cyclization of unactivated alkene with Langlois reagent as a CF 3 source is described. A variety polycyclic quinazolinones were successfully synthesized in 52–81% yields under transition metal‐ oxidant‐free conditions. The used this strategy possesses the advantages bench‐stablity, cost‐effectivity high‐efficiency. Additionally, gram‐scale reaction, broad substrate scope good functional group tolerance demonstrated synthetic usefulness protocol. magnified image

Language: Английский

Citations

36

Divergent electrolysis for the controllable coupling of thiols with 1,2-dichloroethane: a mild approach to sulfide and sulfoxide DOI
Fei Ling, Tao Liu, Chao Xu

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(3), P. 1342 - 1349

Published: Jan. 1, 2022

Electrocatalysis for the controllable coupling of thiols with DCE was achieved to generate value-added β-chloro-tethered sulfur compounds in batch and flow.

Language: Английский

Citations

30