4.6 Article

Electrochemical NaI-mediated one-pot synthesis of guanidines from isothiocyanates via tandem addition-guanylation

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Organic

Migration from Photochemistry to Electrochemistry for [2+2] Cycloaddition Reaction

Issa Yavari et al.

Summary: In this study, a novel electrochemical approach for synthesizing cyclobutanes through a simple [2+ 2] cycloaddition reaction of two electron-deficient olefins in the absence of photocatalysts or metal catalysts is introduced based on the principles of electrosynthesis technique. This electrochemical strategy provides suitable conditions for synthesizing tetrasubstituted cyclobutanes with various functional groups in good to excellent efficiency, compatible with large-scale synthesis. This approach emphasizes the convenience of reaction instruments and starting materials, and readily accessible and inexpensive electrode materials serve as strong evidence of the simplicity of this reaction. Mechanistic insights into the reaction are obtained through investigation of the cyclic voltammetry spectra of the reactants, and the structure of a product is identified using X-ray crystallography.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

Electrochemical Isothiocyanation of Primary Amines

Cyrille Kiaku et al.

Summary: In this study, a new practical electrochemical method for the synthesis of aliphatic and aromatic isothiocyanates from amine and carbon disulfide is reported. The method is mild, high-yielding, and does not require the use of supporting electrolytes, making it a convenient and cost-effective alternative to classical syntheses.

ORGANIC LETTERS (2023)

Review Chemistry, Organic

Recent Advances in Electrochemical Cascade Cyclization Reactions

Cai Zhang et al.

Summary: This review article summarizes recent developments in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, including pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-a]pyridines, imidazoles, etc. The works reported from 2012 to 2022 are divided into two major sections: heterocycle construction and carbocycle construction reactions.

SYNTHESIS-STUTTGART (2023)

Article Chemistry, Organic

Metal-Free Synthesis of Guanidines from Thioureas in Water Reactions Mediated by Visible Light

Rose Malina Annuur et al.

Summary: A metal-free synthesis of guanidines from thioureas under visible-light irradiation in water was successfully developed. By using a photocatalyst and a surfactant with an additive base, conversions of various thioureas into guanidines were achieved in moderate to high yields. The advantages of this reaction include the use of a metal-free photocatalyst, water as a nontoxic solvent, and ease of operation at room temperature in an open-flask manner.

SYNTHESIS-STUTTGART (2023)

Review Chemistry, Multidisciplinary

A practical guide to electrosynthesis

Matthew C. Leech et al.

Summary: Organic electrosynthesis is an important discipline that utilizes electricity for redox reactions. This Review covers the fundamental aspects of the field, practical tips, and the basics of electroanalytical techniques.

NATURE REVIEWS CHEMISTRY (2022)

Article Chemistry, Organic

Electrochemical Amidation: Benzoyl Hydrazine/Carbazate and Amine as Coupling Partners

Tipu Alam et al.

Summary: An electrochemical reaction was utilized to couple benzoyl hydrazine/carbazate and primary/secondary amine, resulting in the cleavage and formation of C(sp(2))-N bonds. This method is metal-free and does not require an external oxidant, producing N-2 and H-2 as byproducts. Mechanistic studies discovered the in situ generation of acyl and N-centered radicals from benzoyl hydrazines and amines. The usefulness of this approach was demonstrated through the large-scale synthesis of bezafibrate, a hyperlipidemic drug.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Electrochemical Synthesis of N-Acyl/Sulfonylsulfenamides Using Potassium Iodide as Mediator

Wei Zhaoxin et al.

Summary: An efficient and environmentally friendly electrocatalytic protocol has been developed for synthesizing N-acyl/ sulfonyl sulfenamides. Various electron-deficient groups substituted amines and aryl thiols react smoothly to afford the N-S bond formation products in yields ranging from 36% to 98%. Preliminary mechanistic studies suggest the reaction may proceed through a free radical process.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

De novo design and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions

Yameng Wan et al.

Summary: This study presents the de novo design and synthesis of a new class of visible-light photoredox catalysts, which showed high efficiency in the guanylation of various substrates. The method offers broad substrate scope, functional group tolerance, and the potential for late-stage derivatizations to produce compounds with significant anticancer activity.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition-cyclization

Thao Nguyen Thanh Huynh et al.

Summary: An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates using NaI and NaCl as catalysts in an open-flask undivided cell provides various products in moderate to high yields. This method is also applicable to the synthesis of 2-aminobenzothiazoles and has the benefits of being metal-free, scalable, and environmentally friendly.

GREEN CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

A Survival Guide for the Electro-curious

Cian Kingston et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Physical

Electrochemical oxidative aminocarbonylation of terminal alkynes

Li Zeng et al.

NATURE CATALYSIS (2020)

Review Chemistry, Multidisciplinary

Electrode Materials in Modern Organic Electrochemistry

David M. Heard et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Organic

A Mild Photocatalytic Synthesis of Guanidine from Thiourea under Visible Light

Trin Saetan et al.

ORGANIC LETTERS (2020)

Review Chemistry, Multidisciplinary

Organic electrosynthesis: from academia to industry

Matthew C. Leech et al.

REACTION CHEMISTRY & ENGINEERING (2020)

Review Chemistry, Multidisciplinary

Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Reactions

Yong Yuan et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Article Chemistry, Multidisciplinary

Electrochemical Synthesis of Imidazo-Fused N-Heteroaromatic Compounds through a C-N Bond-Forming Radical Cascade

Zhong-Wei Hou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Electrochemical synthesis of 1,2,4-triazole-fused heterocycles

Zenghui Ye et al.

GREEN CHEMISTRY (2018)

Review Chemistry, Organic

Recent advances in iodine mediated electrochemical oxidative cross-coupling

Kun Liu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Article Chemistry, Physical

An Electrocatalytic Approach to the Radical Difunctionalization of Alkenes

Gregory S. Sauer et al.

ACS CATALYSIS (2018)

Article Chemistry, Medicinal

Antileishmanial Thioureas: Synthesis, Biological Activity and in Silico Evaluations of New Promising Derivatives

Gil Mendes Viana et al.

CHEMICAL & PHARMACEUTICAL BULLETIN (2017)

Review Chemistry, Multidisciplinary

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Ming Yan et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Updating and further expanding GSK's solvent sustainability guide

Catherine M. Alder et al.

GREEN CHEMISTRY (2016)

Article Chemistry, Organic

Simple and efficient methodology to prepare guanidines from 1,3-disubstituted thioureas

Marcio V. Costa et al.

TETRAHEDRON LETTERS (2016)

Article Chemistry, Organic

Ultrasound-assisted synthesis of substituted guanidines from thioureas

Mookda Pattarawarapan et al.

TETRAHEDRON LETTERS (2016)

Article Chemistry, Multidisciplinary

Synthetic Organic Electrochemistry: An Enabling and Innately Sustainable Method

Evan J. Horn et al.

ACS CENTRAL SCIENCE (2016)

Review Chemistry, Multidisciplinary

Guanidines: from classical approaches to efficient catalytic syntheses

Carlos Alonso-Moreno et al.

CHEMICAL SOCIETY REVIEWS (2014)

Article Chemistry, Inorganic & Nuclear

Clicking thiourea into a salen scaffold: Structures and cytotoxicity of cobalt(II) and nickel (II) complexes

Guoqi Zhang et al.

INORGANIC CHEMISTRY COMMUNICATIONS (2014)

Article Chemistry, Organic

A Mild Method for the Synthesis of Carbamate-Protected Guanidines Using the Burgess Reagent

Toshikatsu Maki et al.

ORGANIC LETTERS (2014)

Article Chemistry, Applied

Efficient Indirect Electrochemical Synthesis of 2-Substituted Benzoxazoles using Sodium Iodide as Mediator

Wei-Cui Li et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

Article Cardiac & Cardiovascular Systems

Effects of KATP channel openers diazoxide and pinacidil in coronary-perfused atria and ventricles from failing and non-failing human hearts

Vadim V. Fedorov et al.

JOURNAL OF MOLECULAR AND CELLULAR CARDIOLOGY (2011)

Article Chemistry, Multidisciplinary

Organic electrosynthesis: a promising green methodology in organic chemistry

Bernardo A. Frontana-Uribe et al.

GREEN CHEMISTRY (2010)

Article Chemistry, Organic

The first bismuth(III)-catalyzed guanylation of thioureas

Silvio Cunha et al.

TETRAHEDRON LETTERS (2006)

Article Chemistry, Applied

Solution- and solid-phase syntheses of substituted guanidinocarboxylic acids

J Chen et al.

JOURNAL OF COMBINATORIAL CHEMISTRY (2000)