Direct C-H Arylation of Quinones with Anilines

Lamblin, Marc; Naturale, Guillaume; Dessolin, Jean; Felpin, François‐Xavier

doi:10.1055/s-0031-1291163

Cited by 32 publications

(20 citation statements)

References 8 publications

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“…ArQs are usually prepared by the addition reaction of the diazonium salts of Ar with quinones, which is known as the Meerwein arylation, a classic method, and the aryl‐coupling reaction of halogenated quinones with the boronic acid ester of Ar in the presence of a transition metal catalyst, which is known as the Suzuki‐Miyaura coupling, a contemporary method . However, considering the instability of the unsubstituted biphenoquinone and the low solubilities of the corresponding halogenated biphenoquinones, the application of the Meerwein arylation and the Suzuki‐Miyaura coupling seemed to be difficult.…”

Section: Resultsmentioning

confidence: 99%

Pyren‐2‐yl‐Substituted Biphenoquinone and p‐Benzoquinone: Pyren‐2‐yl as a Weak Electron‐Withdrawing Substituent

2016

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Pyren‐2‐yl‐substituted biphenoquinone and p‐benzoquinone were designed and synthesized by oxidizing 2,6‐bis(pyren‐2‐yl)phenol with PbO2 in acetic acid. The molecules showed properties characteristic of biphenoquinone and p‐benzoquinone, i. e., reduction processes and light absorption in the visible region. In electrochemistry, the positively shifted reduction potentials suggest that pyren‐2‐yl could act as an electron‐withdrawing substituent although the substitution position of the pyrene is the node of its frontier orbital. The biphenoquinone derivative underwent the thermal reductive disproportionation reaction to afford corresponding hydroquinones and furan annulated π‐expanded compounds.

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Section: Resultsmentioning

confidence: 99%

Pyren‐2‐yl‐Substituted Biphenoquinone and p‐Benzoquinone: Pyren‐2‐yl as a Weak Electron‐Withdrawing Substituent

2016

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“…In 2012, Lamblin and Felpin found that a mixture of anilines and t BuONO in aqueous DMSO led to the formation of corresponding diazonium hydroxides. With this observation, the arylation reactions of benzoquinone with in situ generated diazonium hydroxides from anilines and t BuONO were carried out (Scheme ) . This approach avoided the preparation and handling of explosive diazonium salt, and no corrosive HCl was needed.…”

Section: Arylation Of Quinonesmentioning

confidence: 99%

Recent Advances in Direct Functionalization of Quinones

2019

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Developing methods for the direct functionalization of quinones for assembly of highly functionalized quinones or bioactive natural products is an essential topic in the field of direct C–H functionalization. Quinone units are key motifs in many bioactive compounds and materials, and many innovative methods have been elaborated for the generation of these units. A major part of the established synthetic strategies combines installation of substituents on hydroquinones, phenols, or phenyl ethers through different coupling reactions with oxidation to produce the desired quinones. Most of these above‐mentioned methods introduce multiple chemical steps; however, the synthesis of quinoid compounds through the direct C–H functionalization of simple quinones remains challenging. This minireview summarizes the recently developed achievements for assembly of functionalized quinones through direct functionalization of simple quinones. Our focus will be on the methods and mechanism of these reactions that have appeared in the last two decades.

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“…101,259-267 Lamblin et al 268 developed a facile route for 2-aryl-1,4benzoquinones (142) via direct C-H arylation of p-quinone (11) with anilines (24) in the presence of tert-butyl nitrite in aqueous DMSO at room temperature under neutral, additive-free and metal-free conditions (Scheme 50). 101,259-267 Lamblin et al 268 developed a facile route for 2-aryl-1,4benzoquinones (142) via direct C-H arylation of p-quinone (11) with anilines (24) in the presence of tert-butyl nitrite in aqueous DMSO at room temperature under neutral, additive-free and metal-free conditions (Scheme 50).…”

Section: Scheme 49 Cobalt Acetylacetonate-catalyzed Synthesis Of Submentioning

confidence: 99%

Design for carbon–carbon bond forming reactions under ambient conditions

Brahmachari

2016

RSC Adv.

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Carbon-carbon (C-C) bond forms the 'backbone' of nearly every organic molecule, and lies at the heart of the chemical sciences! This transformation has always been one of the most useful and fundamental reactions in the development of organic chemistry. Currently, the concept of 'green chemistry' is globally acclaimed and has already advanced quite significantly to come out as a distinct branch of chemical sciences. Among the principles of 'green chemistry', one principle is dedicated to "design of energy efficiency" -that is to develop synthetic strategies that require less/minimum amount of energy to carry out a specific reaction with optimum productivity. And the most effective way-out to save energy is to develop strategies/protocols that are capable enough to carry out the transformations at ambient temperature and pressure! As part of on-going developments on green synthetic strategies, designing for reactions under ambient conditions coupled with other green aspects is, thus, an area of current choice. This review is aimed to offer an up-to-date development on the design of carbon-carbon bond forming protocols to access a wide variety of organic molecules of topical significance under ambient conditions. The account highlights on the brilliant applications of reaction conditions such as the use of solvents or no solvent, catalysts or no catalyst, and the use of green tools like ball-milling, ultrasonication and visible light in achieving the goal! Design for Carbon Carbon Frameworks at Ambient ConditionsN Me Me Me O O COOH Br Br (Graphic for TOC)

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Direct C-H Arylation of Quinones with Anilines

Cited by 32 publications

References 8 publications

Pyren‐2‐yl‐Substituted Biphenoquinone and p‐Benzoquinone: Pyren‐2‐yl as a Weak Electron‐Withdrawing Substituent

Pyren‐2‐yl‐Substituted Biphenoquinone and p‐Benzoquinone: Pyren‐2‐yl as a Weak Electron‐Withdrawing Substituent

Recent Advances in Direct Functionalization of Quinones

Design for carbon–carbon bond forming reactions under ambient conditions

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