Manganese‐Mediated Electrooxidative Ring‐Opening Azidation of Cyclobutanol Derivatives with TMSN3 DOI
Wenchao Gao, Jie Yang,

Yong Teng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2501 - 2506

Published: April 17, 2024

Abstract A Mn‐electrocatalytic ring‐opening azidation of tert ‐cyclobutanols has been developed. The regioselective method is applicable for the a diverse array cyclobutanols to provide practical γ ‐azido ketones in 23–91% yields under chemical oxidants‐free reaction conditions. Detailed mechanistic studies suggest process Mn‐mediated alkoxy radical generation followed by β ‐scission form carbon‐centered species possibly involved this transformation.

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

141

Electrochemical chemoselective thiocarbamylation of late-stage Tyr-containing drugs and peptides DOI

Wan‐Jie Wei,

Xinyu Wang, Haitao Tang

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(10), P. 3382 - 3388

Published: Aug. 2, 2024

Language: Английский

Citations

24

Tryptophan-specific modification and diversification of peptides and proteins DOI
S K Kundu, A. Bandyopadhyay, Rajib Sarkar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review provides an account of the tryptophan-specific conjugation peptides and proteins its extensive application in imaging living cells, radiolabelling proteins, protein engineering, etc .

Language: Английский

Citations

2

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

Xinyue Fang,

Yong Zeng,

Yawen Huang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: June 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.

Language: Английский

Citations

11

Manganese-Catalyzed Electrochemical Oxidation of Tryptophan-Containing Peptides and Indole Derivatives by O2 DOI
Min Xu, Qin He, Xiaojiang Li

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3928 - 3939

Published: Feb. 20, 2025

Language: Английский

Citations

1

An electrochemical multicomponent reaction toward C–H tetrazolation of alkyl arenes and vicinal azidotetrazolation of alkenes DOI Creative Commons
Yi Yu,

Xiao-Bin Zhu,

Yaofeng Yuan

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(46), P. 13851 - 13856

Published: Jan. 1, 2022

An electrochemical multicomponent reaction (e-MCR) enables highly efficient and selective C–H tetrazolation of alkyl arenes, vicinal azidotetrazolation alkenes, with readily available acetonitrile azidotrimethylsilane.

Language: Английский

Citations

31

Chiral Aldehyde–Palladium Catalysis Enables Asymmetric Synthesis of α-Alkyl Tryptophans via Cascade Heck-Alkylation Reaction DOI

Qi-Wen Shen,

Wen Wei,

Qi‐Xiang Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(17), P. 3163 - 3167

Published: April 25, 2023

The first catalytic asymmetric cascade Heck-alkylation reaction of NH2-unprotected amino acid esters with N-(2-iodophenyl)allenamides is reported in this work. Under the promotion a combining system comprising chiral aldehyde, palladium complex, and Lewis ZnCl2, title takes place smoothly, giving optically active α-alkyl tryptophan derivatives moderate to good yields excellent enantioselectivities. target products can be converted into other structurally complex indoles without loss

Language: Английский

Citations

17

Recent Progress in Electrochemical Modification of Amino Acids and Peptides DOI

Xinyue Fang,

Yawen Huang,

Xinwei Hu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 903 - 903

Published: Jan. 1, 2024

Language: Английский

Citations

7

Electrochemical cascade reactions: an account of recent developments for this modern strategic tool in the arsenal of chemical synthesis DOI
Manoj Kumar Yadav, Sushobhan Chowdhury

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(24), P. 10144 - 10181

Published: Jan. 1, 2023

The electrochemical cascade process majorly satisfies the essential criteria of green synthesis. Being an Integrated synthetic strategy it can produce more molecules in a shorter time and thus provides modern strategic tool arsenal chemists.

Language: Английский

Citations

11

A multicomponent reaction for modular assembly of indole-fused heterocycles DOI Creative Commons
Jiaming Li, Hao Ni, Weiwei Zhang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(14), P. 5211 - 5217

Published: Jan. 1, 2024

Indoles are privileged chemical entities in natural products and drug discovery. Indole-fused heterocycles, particularly seven-membered ones, have received increasing attention due to their distinctive characteristics wide spectrum of bioactivities. However, the synthetic access these compounds is highly limited. Herein, we report a unique multicomponent reaction (MCR) for modular assembly indole-fused heterocycles. In this process, indole, formaldehyde amino hydrochloride could assemble rapidly yield oxadiazepines, another addition sodium thiosulphate would furnish thiadiazepines. The biological evaluation disclosed promising anticancer activity compounds. Furthermore, MCR be applicable late-stage selective modifications peptides. Therefore, work provides powerful strategy indole functionalization valuable tool construction

Language: Английский

Citations

4