C–H Amination via Electrophotocatalytic Ritter-type Reaction DOI
Tao Shen, Tristan H. Lambert

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(23), P. 8597 - 8602

Published: June 2, 2021

A method for C–H bond amination via an electrophotocatalytic Ritter-type reaction is described. The catalyzed by a trisaminocyclopropenium (TAC) ion in electrochemical cell under irradiation. These conditions convert benzylic bonds to acetamides without the use of stoichiometric chemical oxidant. range functionality shown be compatible with this transformation, and several complex substrates are demonstrated.

Language: Английский

Electrocatalysis as an enabling technology for organic synthesis DOI
Luiz F. T. Novaes, Jinjian Liu, Yifan Shen

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(14), P. 7941 - 8002

Published: Jan. 1, 2021

Electrochemistry has recently gained increased attention as a versatile strategy for achieving challenging transformations at the forefront of synthetic organic chemistry. Electrochemistry's unique ability to generate highly reactive radical and ion intermediates in controlled fashion under mild conditions inspired development number new electrochemical methodologies preparation valuable chemical motifs. Particularly, recent developments electrosynthesis have featured an use redox-active electrocatalysts further enhance control over selective formation downstream reactivity these intermediates. Furthermore, electrocatalytic mediators enable proceed manner that is mechanistically distinct from purely methods, allowing subversion kinetic thermodynamic obstacles encountered conventional synthesis. This review highlights key innovations within past decade area electrocatalysis, with emphasis on mechanisms catalyst design principles underpinning advancements. A host oxidative reductive are discussed grouped according classification transformation nature electrocatalyst.

Language: Английский

Citations

884

Organic Electrochemistry: Molecular Syntheses with Potential DOI Creative Commons
Cuiju Zhu, Nate W. J. Ang, Tjark H. Meyer

et al.

ACS Central Science, Journal Year: 2021, Volume and Issue: 7(3), P. 415 - 431

Published: March 9, 2021

Efficient and selective molecular syntheses are paramount to

Language: Английский

Citations

590

Electro-organic synthesis – a 21stcentury technique DOI

Dennis Pollok,

Siegfried R. Waldvogel

Chemical Science, Journal Year: 2020, Volume and Issue: 11(46), P. 12386 - 12400

Published: Jan. 1, 2020

This perspective provides insight into recent electro-organic methods and general trends in this field, opens up prospects for future viewpoints.

Language: Английский

Citations

528

C–H activation DOI
Torben Rogge, Nikolaos Kaplaneris, Naoto Chatani

et al.

Nature Reviews Methods Primers, Journal Year: 2021, Volume and Issue: 1(1)

Published: June 17, 2021

Language: Английский

Citations

440

Powering the Future: How Can Electrochemistry Make a Difference in Organic Synthesis? DOI Creative Commons
Tjark H. Meyer, Isaac Choi, Cong Tian

et al.

Chem, Journal Year: 2020, Volume and Issue: 6(10), P. 2484 - 2496

Published: Sept. 24, 2020

Language: Английский

Citations

383

New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry DOI Creative Commons
Jinjian Liu, Lingxiang Lu, Devin Wood

et al.

ACS Central Science, Journal Year: 2020, Volume and Issue: 6(8), P. 1317 - 1340

Published: July 16, 2020

As the breadth of radical chemistry grows, new means to promote and regulate single-electron redox activities play increasingly important roles in driving modern synthetic innovation. In this regard, photochemistry electrochemistry-both considered as niche fields for decades-have seen an explosive renewal interest recent years gradually have become a cornerstone organic chemistry. Outlook article, we examine current state-of-the-art areas electrochemistry photochemistry, well nascent area electrophotochemistry. These techniques employ external stimuli activate molecules imbue privileged control reaction progress selectivity that is challenging traditional chemical methods. Thus, they provide alternative entries known reactive intermediates enable distinct strategies were previously unimaginable. Of many hallmarks, electro- are often classified "green" technologies, promoting reactions under mild conditions without necessity potent wasteful oxidants reductants. This reviews most growth these with special emphasis on conceptual advances given rise enhanced accessibility tools trade.

Language: Английский

Citations

377

Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis DOI
Christian A. Malapit,

Matthew B. Prater,

Jaime R. Cabrera‐Pardo

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(3), P. 3180 - 3218

Published: Nov. 19, 2021

Synthetic organic electrosynthesis has grown in the past few decades by achieving many valuable transformations for synthetic chemists. Although electrocatalysis been popular improving selectivity and efficiency a wide variety of energy-related applications, last two decades, there much interest to develop conceptually novel transformations, selective functionalization, sustainable reactions. This review discusses recent advances combination electrochemistry homogeneous transition-metal catalysis synthesis. The enabling mechanistic studies are presented alongside advantages as well future directions address challenges metal-catalyzed electrosynthesis.

Language: Английский

Citations

306

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

296

Making electrochemistry easily accessible to the synthetic chemist DOI Creative Commons

Christiane Schotten,

Thomas P. Nicholls, Richard A. Bourne

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(11), P. 3358 - 3375

Published: Jan. 1, 2020

This tutorial bridges an important knowledge gap by providing easily accessible introduction that enables synthetic chemists to explore electrochemistry.

Language: Английский

Citations

277

Manganese-Catalyzed Oxidative Azidation of C(sp3)–H Bonds under Electrophotocatalytic Conditions DOI
Linbin Niu,

Chongyu Jiang,

Yuwei Liang

et al.

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(41), P. 17693 - 17702

Published: Sept. 17, 2020

The selective installation of azide groups into C(sp3)-H bonds is a priority research topic in organic synthesis, particularly pharmaceutical discovery and late-stage diversification. Herein, we demonstrate generalized manganese-catalyzed oxidative azidation methodology using nucleophilic NaN3 as an source under electrophotocatalytic conditions. This approach allows us to perform the reaction without necessity adding excess substrate successfully avoiding use stoichiometric chemical oxidants such iodine(III) reagent or NFSI. A series tertiary secondary benzylic C(sp3)-H, aliphatic drug-molecule-based substrates are well tolerated our protocol. simultaneous gram-scale synthesis ease transformation amine collectively advocate for potential application preparative synthesis. Good reactivity bond selectivity incorporate nitrogen-based functionality at alkyl group also provide opportunities manipulate numerous medicinal candidates. We anticipate synthetic protocol, consisting metal catalysis, electrochemistry, photochemistry, would new sustainable option execute challenging transformations.

Language: Английский

Citations

261