Electrochemical Late-Stage Functionalization

Chemical Reviews, Год журнала: 2023, Номер 123(19), С. 11269 - 11335

Опубликована: Сен. 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.

Язык: Английский

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Recent developments in the cleavage, functionalization, and conjugation of proteins and peptides at tyrosine residues

Chemical Science, Год журнала: 2023, Номер 14(29), С. 7782 - 7817

Опубликована: Янв. 1, 2023

Peptide and protein selective modification at tyrosine residues has become an exploding field of research as constitutes a robust alternative to lysine cysteine-targeted traditional peptide/protein protocols. This review offers comprehensive summary the latest advances in tyrosine-selective cleavage, functionalization, conjugation peptides proteins from past three years. updated overview complements extensive body work on site-selective proteins, which holds significant relevance across various disciplines, including chemical, biological, medical, material sciences.

Язык: Английский

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Diversification of pharmaceutical molecules via late-stage C(sp2)–H functionalization

Green Synthesis and Catalysis, Год журнала: 2023, Номер 4(2), С. 104 - 123

Опубликована: Янв. 2, 2023

C–H late-stage functionalization has gradually become a powerful approach for the rapid optimization of lead compounds' bioactivity. Significant advances in this field have been achieved past few years, mainly, system (hetero)aryl activation owing to importance moiety pharmaceutical. In review, we described selected recent examples how developed intermolecular C(sp2)–H methodologies involving diverse techniques diversify pharmaceutical molecules late stage.

Язык: Английский

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Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июнь 18, 2024

Abstract Peptide aldehydes are crucial biomolecules essential to various biological systems, driving a continuous demand for efficient synthesis methods. Herein, we develop metal-free, facile, and biocompatible strategy direct electrochemical of unnatural peptide aldehydes. This electro-oxidative approach enabled step- atom-economical ring-opening via C‒N bond cleavage, allowing homoproline-specific diversification expansion substrate scope include amides, esters, cyclic amines sizes. The remarkable efficacy the electro-synthetic protocol set stage modification assembly linear macrocyclic peptides using concise synthetic sequence with racemization-free conditions. Moreover, combination experiments density functional theory (DFT) calculations indicates that different N -acyl groups play decisive role in reaction activity.

Язык: Английский

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The crucial role of silver(i)-salts as additives in C–H activation reactions: overall analysis of their versatility and applicability

Chemical Society Reviews, Год журнала: 2023, Номер 52(18), С. 6359 - 6378

Опубликована: Янв. 1, 2023

This review discusses the important role of silver( i ) salts as additives in transition-metal catalyzed C–H activation, and depicts discussion about current shift towards Ag-free procedures, plausible sustainable alternatives.

Язык: Английский

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Recent Progress in Electrochemical Modification of Amino Acids and Peptides

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(3), С. 903 - 903

Опубликована: Янв. 1, 2024

Язык: Английский

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Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations

ChemCatChem, Год журнала: 2024, Номер 16(14)

Опубликована: Фев. 7, 2024

Abstract This review delves into the innovative field of interfacial photoelectrochemical (iPEC) and (PEC) catalysis, dynamic synthesis methodologies that seamlessly integrates electrochemical photoredox catalysis for efficient environmentally friendly reactions. Utilizing minute quantities photocatalysts, visible light becomes a powerful tool, generating transient excited states to catalyze spectrum reactions through single‐electron oxidation or reduction events. The categorizes recent advancements, highlighting applications in organic synthesis, late‐stage modifications, distinctive features methodology. Despite being its early stages, this synergistic approach holds great promise propelling forward, with potential large‐scale diverse functionalizations, including asymmetric bioconjugation strategies biomolecule modifications.

Язык: Английский

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The thiol-sulfoxonium ylide photo-click reaction for bioconjugation

Chemical Science, Год журнала: 2022, Номер 14(3), С. 604 - 612

Опубликована: Дек. 3, 2022

Visible-light-mediated methods were heavily studied as a useful tool for cysteine-selective bio-conjugation; however, many current suffer from bio-incompatible reaction conditions and slow kinetics. To address these challenges, herein, we report transition metal-free thiol-sulfoxonium ylide photo-click that enables bioconjugation under bio-compatible conditions. The is highly generally finished within minutes with naturally occurring riboflavin derivatives organic photocatalysts. catalysts substrates are readily accessible bench stable have satisfactory water solubility. As proof-of-concept study, the was smoothly applied in chemo-proteomic analysis, which provides efficient tools to explore druggable content of human proteome.

Язык: Английский

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Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

ChemSusChem, Год журнала: 2023, Номер 16(12)

Опубликована: Март 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.

Язык: Английский

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

ChemistrySelect, Год журнала: 2023, Номер 8(11)

Опубликована: Март 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.

Язык: Английский

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