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

Photo‐Induced C−H Methylation Reactions DOI

Qian‐Yu Li,

Yuhang He, Yu‐Mei Lin

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(72)

Published: Oct. 6, 2023

Direct C-H methylation is a highly valuable approach for introducing methyl groups into organic molecules, particularly in pharmaceutical chemistry. Among the various methodologies available, photo-induced stands out as an exceptional choice due to its mild reaction conditions, energy efficiency, and compatibility with functional groups. This article offers comprehensive review of photochemical strategies employed direct selective C(sp3 )-H, C(sp2 C(sp)-H bonds molecules. The discussed encompass transition-metal-based photocatalysis, organophotocatalysis, well other metal-free approaches, including electron donor-acceptor (EDA)-enabled transformations. Importantly, wide range easily accessible agents such tert-butyl peroxide, methanol, DMSO, ether, TsOMe, N-(acetoxy)phthalimide, acetic acid, halides, even methane can serve effective methylating reagents modifying diverse targets. These advancements are anticipated drive further progress fields synthesis, development, opening up exciting avenues creating novel molecules discovering new drug compounds.

Language: Английский

Citations

9

Convenient Preparation of N-Acylbenzoxazines from Phenols, Nitriles, and DMSO Initiated by a Catalytic Amount of (COCl)2 DOI
Hao Wang,

Zeyu Xi,

Shuai Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(7), P. 4932 - 4943

Published: March 17, 2021

A convenient preparation method of N-acylbenzoxazines has been developed, in which phenols react with nitriles and dimethyl sulfoxide (DMSO) the presence a catalytic amount (COCl)2 CH3CN or chloroform to afford corresponding moderate-to-good yields. DMSO acts as source HCHO, is generated situ from decomposition methoxydimethylsulfonium salt. regeneration cycle salt proposed, initiated by (COCl)2.

Language: Английский

Citations

16

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis DOI Creative Commons
Peng Wu,

Gabriel Goujon,

Shulei Pan

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(51)

Published: Sept. 5, 2024

Benzo[1,3,2]dithiazole-1,1,3-trioxides are bench-stable and easy-to-use reagents. In photoredox catalysis, they generate methyl perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, N-Ts acrylamide. As byproduct, salt is formed be regenerated the original methylating agent. Flow chemistry provides an option for reaction scale-up further underscoring synthetic usefulness these methylation Mechanistic investigations suggest single-electron transfer (SET) pathway induced by catalysis.

Language: Английский

Citations

2

Hydrogen-Transfer-Mediated N-Arylation of Naphthols Using Indolines as Hydrogen Donors DOI
Xiuwen Chen,

Zhihai Yang,

Xuyan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 85(2), P. 508 - 514

Published: Nov. 29, 2019

Using a hydrogen-transfer-mediated activation mode, we report new catalytic system for the transfer hydrogenation of naphthols. In presence Pd/C catalyst and base, various naphthols reacted with indolines to afford N-aryl-substituted heterocyclic compounds. Indolines were found act as novel hydrogen donors under palladium catalysis. This method features good functional tolerance, operational simplicity, readily available catalyst.

Language: Английский

Citations

18

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

Citations

10