Electrochemical Ruthenium‐Catalysed Directed C−H Functionalization of Arenes with Boron Reagents DOI
J. Kenyon, Igor Larrosa

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(4), P. 830 - 837

Published: Dec. 19, 2023

Abstract Ortho ‐directed electrochemical C−H functionalization of aromatics with boron‐based coupling partners has been achieved under ruthenium catalysis through an oxidatively induced reductive elimination mechanism. Our method provides a single set conditions delivering arylation, alkenylation and methylation, yielding ortho ‐functionalized products good functional group tolerance, including examples late‐stage in synthetically useful yields. By harnessing electricity as ‘green’ oxidant, this circumvents the need for stoichiometric quantities chemical oxidants, enhancing our sustainability metrics.

Language: Английский

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

144
Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis DOI
Prabhat Kumar Baroliya, Mukesh Dhaker, Subir Panja

et al.

ChemSusChem, Journal Year: 2023, Volume and Issue: 16(12)

Published: March 7, 2023

Electrochemically promoted transition metal-catalyzed C-H functionalization has emerged as a promising area of research over the last few decades. However, development in this field is still at an early stage compared to traditional reactions using chemical-based oxidizing agents. Recent reports have shown increased attention on electrochemically functionalization. From standpoint sustainability, environmental friendliness, and cost effectiveness, oxidation metal catalyst offers mild, efficient, atom-economical alternative chemical oxidants. This Review discusses advances metal-electrocatalyzed past decade describes how unique features electricity enable economic sustainable way.

Language: Английский

Citations

13
Demystifying the recent photochemical and electrochemical tricks on installing the magic methyl group: A comprehensive overview DOI

Feiyang Liao,

Zenghui Wei,

Yunhao Guan

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(14), P. 8161 - 8203

Published: Jan. 1, 2024

The strategic installation of the “magic methyl” group has become highly desirable for drug discovery. This review summarized recent photochemical and electrochemical strategies in installing methyl group.

Language: Английский

Citations

4
Electrochemically driven oxidative C–H/N–H cross-coupling reactions of cyclic sulfamidate imines with primary anilines and secondary amines DOI
Haixia Wang,

Zhi-Hao Li,

Wanwan Li

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(21), P. 8377 - 8385

Published: Jan. 1, 2022

An efficient and eco-friendly electrochemical synthesis of various cyclic N -sulfonylamidines from sulfamidate imines amines via oxidative C–H/N–H cross-coupling under mild reaction conditions has been developed.

Language: Английский

Citations

18
Catalyst-free benzylic C(sp3)–H cross-coupling with organotrifluoroborates enabled by electrochemistry DOI
Chao Li, Ran Ding,

Heng-Yi Guo

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(20), P. 7883 - 7888

Published: Jan. 1, 2022

An electrochemical benzylic C(sp 3 )–H cross-coupling with organotrifluoroborates without any catalyst or external electrolyte has been developed.

Language: Английский

Citations

15
Electrooxidative iridium-catalyzed sp2 C−H activation-annulation leading to cationic π-extended heteroaromatics DOI
Qi‐Liang Yang, Nana Guo,

Shu-Xian Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4849 - 4856

Published: Jan. 1, 2024

An electrochemically driven, Cp*Ir( iii )-catalyzed method for alkenyl and aromatic C(sp 2 )–H activation coupling with alkynes the synthesis of biologically useful quaternary ammonium salts under mild conditions is demonstrated.

Language: Английский

Citations

3
Hydrogen evolution-enabled rhodaelectro-catalyzed [4+2] annulations of purines and 7-deazapurines with alkynes DOI
Chao Xu, Zhensheng Zhang, Tao Liu

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(68), P. 9508 - 9511

Published: Jan. 1, 2022

A series of polycyclic purinium and 7-deazapurinium salts were obtained via rhodaelectro-catalyzed [4+2] annulations with H 2 evolution.

Language: Английский

Citations

13
Regiodivergent Synthesis of Brominated Pyridylthiophenes by Overriding the Inherent Substrate Bias DOI
Kentaro Okano, Masahiro Hosoya, Atsunori Mori

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 431 - 436

Published: June 5, 2023

Abstract A regiocontrolled functionalization of a pyridylthiophene scaffold was accomplished. Regioselectivity for deprotonation the switched by changing reaction conditions, including metal amide base and solvent. Subsequently, in situ transmetalation halogen dance on corresponding organometallic species were controlled additives temperature, as well above conditions. This method successfully enabled synthesis four iodinated constitutional isomers from single starting material, 2-(5-bromo-2-thienyl)pyridine.

Language: Английский

Citations

7
Photocatalyst-free visible-light-induced highly selective acylation of purine nucleosides at the C6 position DOI
Luohao Li,

Huiqin Zheng,

Feixiang Guo

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(26), P. 3910 - 3913

Published: Jan. 1, 2023

A protocol for visible-light-induced C-H acylation selectively at the C6 position of purine nucleosides with aldehydes under photocatalyst-free conditions was established herein. This allows green, mild, and efficient functionalization various a broad range alkyl aryl aldehydes.

Language: Английский

Citations

6
Electrochemical Ruthenium‐Catalysed Directed C−H Functionalization of Arenes with Boron Reagents DOI
J. Kenyon, Igor Larrosa

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(4), P. 830 - 837

Published: Dec. 19, 2023

Abstract Ortho ‐directed electrochemical C−H functionalization of aromatics with boron‐based coupling partners has been achieved under ruthenium catalysis through an oxidatively induced reductive elimination mechanism. Our method provides a single set conditions delivering arylation, alkenylation and methylation, yielding ortho ‐functionalized products good functional group tolerance, including examples late‐stage in synthetically useful yields. By harnessing electricity as ‘green’ oxidant, this circumvents the need for stoichiometric quantities chemical oxidants, enhancing our sustainability metrics.

Language: Английский

Citations

1