Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

Advanced Materials, Journal Year: 2023, Volume and Issue: 35(49)

Published: March 25, 2023

Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient atom-economic tools to prepare PAHs under exceedingly mild conditions constitutes a long-term goal. Traditional syntheses largely relied on multistep approaches or the conventional Scholl reaction. However, reactions are inefficient with electron-deficient substrates, require stoichiometric chemical oxidants, typically occur presence strong acid. In sharp contrast, electrochemistry has gained considerable momentum during past decade an alternative for facile straightforward assembly, generally via electro-oxidative dehydrogenative annulation, releasing molecular hydrogen sole byproduct by evolution This review provides overview recent significant advances field electrochemical various until January 2023.

Language: Английский

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Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(26), P. 5163 - 5229

Published: Jan. 1, 2022

In recent years, there has been a gradual shift from traditional methodologies to electrochemically mediated organic synthesis. The present review outlines the utility of strategies in heterocylic

Language: Английский

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Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

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

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Pyrimidine-directed metal-free C–H borylation of 2-pyrimidylanilines: a useful process for tetra-coordinated triarylborane synthesis

Chemical Science, Journal Year: 2021, Volume and Issue: 12(34), P. 11447 - 11454

Published: Jan. 1, 2021

We present the metal-free ortho -C–H borylation of 2-pyrimidylanilines to afford synthetically important boronic esters and tetra-coordinated triarylboranes, which could be useful in materials science as well Lewis-acid catalysts.

Language: Английский

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Recyclable and reusablen-Bu₄NBF₄/PEG-400/H₂O system for electrochemical C-3 formylation of indoles with Me₃N as a carbonyl source

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(11), P. 4107 - 4113

Published: Jan. 1, 2021

An eco-friendly electrochemical C-3 formylation of indoles using Me₃N as a carbonyl donor in recyclable reaction medium has been developed.

Language: Английский

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Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(11)

Published: March 14, 2023

Abstract The combination of organometallic C−H activation and electro‐catalysis has emerged as a potent synthetic technique for various molecular scaffolds since it avoids the use harmful expensive chemical oxidants in stoichiometric amounts. Moreover, pre‐functionalization substrates is not required newer ways to perform metal‐catalyzed reactions are possible. Here, we have discussed eletrochemically driven acyloxylation, acetoxylation, oxygenation, acylation, amination, alkylation, halogenation, olefinations C−H/N−H annulation using transition‐metal‐catalyst such Ru, Rh, Pd, Co, Ni, Ir, Cu, Mn Au by anodic oxidation, followed reductive elimination form corresponding C−O, C−C, C−N C−X (X=Cl, Br, S etc.) bonds. This review covers recent developments transition‐metal‐catalyzed electrochemical from 2007 until 2022.

Language: Английский

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Synthesis of Non-C₂-Symmetric Biaryldiols via Organo-Electro Catalyzed Aryl–Aryl Dehydrogenative Cross-Coupling

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(9), P. 7524 - 7532

Published: Feb. 19, 2025

Despite a few successful examples, controlling the enantioselectivity in asymmetric synthesis of non-C2-symmetric biaryldiols has long been challenging. To address issues and regioselectivity, we introduced novel organoelectrocatalytic strategy enabling aryl-aryl dehydrogenative cross-coupling reactions. Using this approach, valuable were obtained up to 95% yields 97% enantiomeric excesses (ees), these compounds could be further applied as versatile ligands Detailed mechanistic studies supported sequential diradical followed by central-to-axial chirality conversion pathway.

Language: Английский

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Hydrogen evolution-enabled rhodaelectro-catalyzed [4+2] annulations of purines and 7-deazapurines with alkynes

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

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Elektrooxidative Rhodium‐katalysierte [5+2]‐Anellierung durch C‐H/O‐H‐Aktivierung

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 133(12), P. 6490 - 6495

Published: Jan. 20, 2021

Abstract Elektrooxidative Anellierungen mittels übergangsmetallkatalysierter C‐H‐Aktivierung haben sich als eine transformative Strategie für den schnellen Aufbau von fünf‐ und sechsgliedrigen Heterocyclen erwiesen. Im Gegensatz dazu berichten wir hier über die ersten elektrochemischen metallkatalysierten [5+2]‐Cycloadditionen Synthese wertvollen Benzoxepinstrukturen durch C‐H/O‐H‐Aktivierung. Die effiziente Alkinanellierung zeichnet große Anwendungsbreite mit Elektrizität einzigem Oxidationsmittel aus. Mechanistische Studien deuten auf einen Rhodium(III/I)‐Mechanismus hin, welcher Benzoxepin‐koordinierten Rhodium(I)‐Sandwichkomplex Katalysatorruhezustand anodische Reoxidation zu Rhodium(III) verläuft.

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Rh(III)-Catalyzed [3 + 2] Annulation of Aniline Derivatives with Vinylsilanes via C–H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(19), P. 12375 - 12383

Published: Sept. 22, 2021

The Rh(III)-catalyzed reaction of aniline derivatives that contain a pyrimidine directing group with vinylsilanes results in the formation C3-substituted indoline highly regioselective manner via C–H activation/alkene cyclization cascade. mechanistic experiments indicate bond cleavage is not rate-determining step and proceeds six-membered rhodacycle as key catalytic species through pyrimidine-directed electrophilic ortho-C–H rhodation.

Language: Английский

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