A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis DOI Creative Commons
Nian Li, Ruzal Sitdikov, Ajit Prabhakar Kale

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2500 - 2566

Published: Oct. 9, 2024

With the resurgence of electrosynthesis in organic chemistry, there is a significant increase number routes available for late-stage functionalization (LSF) drugs. Electrosynthetic methods, which obviate need hazardous chemical oxidants or reductants, offer unprecedented control reactions through continuous variation applied potential and possibility combination with photochemical processes. This capability substantial advantage performing electrochemical photoelectrochemical LSF. Ultimately, these protocols are poised to become vital component medicinal chemist's toolkit. In this review, we discuss that have been demonstrated be applicable LSF pharmaceutical drugs, their derivatives, natural substrates. We present analyze representative examples illustrate electrochemistry photoelectrochemistry valuable molecular scaffolds.

Language: Английский

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

75
Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis DOI Creative Commons
Chen Zhu, Ajit Prabhakar Kale, Huifeng Yue

et al.

JACS Au, Journal Year: 2021, Volume and Issue: 1(7), P. 1057 - 1065

Published: June 15, 2021

A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well aryl tosylates can be efficiently coupled a series of N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines sulfonamides are also suitable substrates. Interestingly, when benzophenone imine applied in the arylation, product selectivity toward formation amine addressed by base switch. In addition, alternating current mode successfully applied. DFT calculations support facilitated reductive elimination pathway.

Language: Английский

Citations

63
Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature DOI Creative Commons
Ramesh C. Samanta, Julia Struwe, Lutz Ackermann

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(33), P. 14154 - 14159

Published: April 23, 2020

Abstract Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures strong bases, translating into limited substrate scope. Herein, nickel‐catalyzed C−H unactivated 8‐aminoquinoline amides have been realized under exceedingly mild conditions, namely at room temperature, with a base user‐friendly electrochemical setup. This electrocatalyzed alkylation displays functional group tolerance is applicable to both the primary secondary alkylation. Based on detailed mechanistic studies, nickel(II/III/I) catalytic manifold has proposed.

Language: Английский

Citations

51
Electrochemical and Photocatalytic Synthesis of Organic Compounds Utilizing a Greener Approach. A review DOI

Syed Kashif Ali,

Hanan A. Althikrallah, Mustafa S. Alluhaibi

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 559, P. 114087 - 114087

Published: April 1, 2024

Language: Английский

Citations

8
A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis DOI Creative Commons
Nian Li, Ruzal Sitdikov, Ajit Prabhakar Kale

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2500 - 2566

Published: Oct. 9, 2024

With the resurgence of electrosynthesis in organic chemistry, there is a significant increase number routes available for late-stage functionalization (LSF) drugs. Electrosynthetic methods, which obviate need hazardous chemical oxidants or reductants, offer unprecedented control reactions through continuous variation applied potential and possibility combination with photochemical processes. This capability substantial advantage performing electrochemical photoelectrochemical LSF. Ultimately, these protocols are poised to become vital component medicinal chemist's toolkit. In this review, we discuss that have been demonstrated be applicable LSF pharmaceutical drugs, their derivatives, natural substrates. We present analyze representative examples illustrate electrochemistry photoelectrochemistry valuable molecular scaffolds.

Language: Английский

Citations

6