C−H Methylation Using Sustainable Approaches DOI Open Access
Ishika Agrawal, Gaurav Prakash, Shaeel A. Al‐Thabaiti

et al.

Catalysts, Journal Year: 2022, Volume and Issue: 12(5), P. 510 - 510

Published: May 2, 2022

C−H methylation of sp2 and sp3 carbon centers is significant in many biological processes. Methylated drug candidates show unique properties due to the change solubility, conformation metabolic activities. Several photo-catalyzed, electrochemical, mechanochemical metal-free techniques that are widely utilized strategies medicinal chemistry for arenes heteroarenes have been covered this review.

Language: Английский

Installing the “magic methyl” – C–H methylation in synthesis DOI Creative Commons
Daniya Aynetdinova, Mia Callens, Harry B. Hicks

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(9), P. 5517 - 5563

Published: Jan. 1, 2021

Following notable cases of remarkable potency increases in methylated analogues lead compounds, this review documents the state-of-the-art C–H methylation technology.

Language: Английский

Citations

185

Transition-metal-free C–S bond cleavage and transformation of organosulfur compounds DOI
Ke Yang, Qin Li, Zhengyi Li

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(36), P. 5343 - 5364

Published: Jan. 1, 2023

The activation and transformation of organic chemical bonds is a fundamental scientific problem. In the past several decades, C-S bond cleavage for construction C-C C-heteroatom has received tremendous attention in chemistry. Although significant progress been made field transition metal strategies, variety novel transition-metal-free strategies have also developed using halogenated reagents, oxidants, acids, bases. Moreover, photochemical electrochemical methods to achieve organosulfur compounds. To date, however, no comprehensive review reported. Therefore, we herein provide major advances compounds, including thioethers, sulfoxides, sulfones, thioacetals, sulfonium salts, sulfur ylides.

Language: Английский

Citations

42

Dimethyl Sulfoxide: Yesterday's Solvent, Today's Reagent DOI
Zahra Tashrifi,

Mohammad Mohammadi Khanaposhtani,

Bagher Larijani

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 362(1), P. 65 - 86

Published: Sept. 20, 2019

Abstract Dimethyl sulfoxide (DMSO) has had a long history of use as polar solvent and active pharmaceutical ingredient in the past decades. However, this decade DMSO attracted attention scientists source oxygen, carbon or sulfur wide range organic reactions. In review, we have summarized classified latest findings area based on applications single dual synthon. magnified image

Language: Английский

Citations

140

The Deuterated “Magic Methyl” Group: A Guide to Site‐Selective Trideuteromethyl Incorporation and Labeling by Using CD3Reagents DOI Creative Commons
Joost Steverlynck, Ruzal Sitdikov, Magnus Rueping

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(46), P. 11751 - 11772

Published: June 2, 2021

Abstract In the field of medicinal chemistry, precise installation a trideuteromethyl group is gaining ever‐increasing attention. Site‐selective incorporation deuterated “magic methyl” can provide profound pharmacological benefits and be considered an important tool for drug optimization development. This review provides structured overview, according to trideuteromethylation reagent, currently established methods site‐selective carbon atoms. addition CD 3 , selective introduction 2 H CDH groups also considered. For all methods, corresponding mechanism scope are discussed whenever reported. As such, this starting point synthetic chemists further advance methodologies. At same time, aims guide chemists, offering them available C−CD formation strategies preparation new or modified drugs.

Language: Английский

Citations

72

DMSO as a Dual Carbon Synthon and Water as Oxygen Donor for the Construction of 1,3,5-Oxadiazines from Amidines DOI
Yi Zhang, Jinqiang Kuang, Xu‐Qiong Xiao

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(10), P. 3960 - 3964

Published: May 3, 2021

A selective and efficient synthesis of diaryl 1,3,5-oxadiazines was established for the first time from simple readily available amidines in wet DMSO. DMSO employed as a dual carbon synthon water offered oxygen atom to construct oxadiazine ring. The reaction involved two new C–N C–O bond formations.

Language: Английский

Citations

37

Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry DOI
Hao Lü, Tong Zhou, Lifen Peng

et al.

Topics in Current Chemistry, Journal Year: 2022, Volume and Issue: 380(6)

Published: Oct. 28, 2022

Language: Английский

Citations

26

Potassium tert-butoxide promoted regioselective deuteration of pyridines DOI
Yan Li,

Chenxu Zheng,

Zhi‐Jiang Jiang

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(21), P. 3497 - 3500

Published: Jan. 1, 2022

A regioselective deuteration at the β- and γ-position of pyridines is reported. Efficient occurred with a combination KOtBu DMSO-d6, replenishing prevailing α-deuteration pyridine systems. Preliminary mechanistic studies suggested that dimsyl carbanion acts as one key intermediates.

Language: Английский

Citations

23

Peroxide-mediated site-specific C–H methylation of imidazo[1,2-a]pyridines and quinoxalin-2(1H)-ones under metal-free conditions DOI

Shengzhou Jin,

Hua Yao,

Sen Lin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 18(2), P. 205 - 210

Published: Nov. 28, 2019

An effective approach to realize the direct methylation of imidazo[1,2-a]pyridines and quinoxalin-2(1H)-ones with peroxides under metal-free conditions is described. In this protocol, serve as both radical initiator methyl source. Methylated imidazopyridines were smoothly synthesized in moderate good yields. A free reaction mechanism was proposed describe process.

Language: Английский

Citations

37

Metal-free C–H methylation and acetylation of heteroarenes with PEG-400 DOI
Vishal Suresh Kudale, Jeh‐Jeng Wang

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(11), P. 3506 - 3511

Published: Jan. 1, 2020

Herein described a novel and an efficient route for the site selective functionalization of aza-heteroarenes using combination PEG-400, O2and TsOH·H2O.

Language: Английский

Citations

34

Recent Progress in Methyl-Radical-Mediated Methylation or Demethylation Reactions DOI
Jiapian Huang, Zhiyuan Chen, Jie Wu

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(17), P. 10713 - 10732

Published: Aug. 13, 2021

Methylation is an important process in biology. To date, radical-type methylation protocols have been developed the late-stage modifications of privileged scaffolds pharmaceutical research and medicinal materials sciences. As a result, chemistry methyl-radical-involved conversions, which was significant topic interest over past few years, has greatly developed. This review focuses on most recent developments catalytic radical or demethylation that were mediated by methyl radicals. We classify reactions according to origination species illustrate diversity radical-based mechanisms; these generation pathways include (1) photo-/electro-catalysis, (2) transition-metal catalysis, (3) transition-metal-free methylations, (4) demethylation-triggered cyclization/cascade reactions. In addition mechanisms, some representative methyl-containing molecules produced from specific are presented analyzed.

Language: Английский

Citations

32