Recent Advances in the Synthesis of Arylamines in the Light of Application in Pharmaceutical and Chemical Industry

Berthold, Dino; Haydl, Alexander M.; Leung, Joyce C.; Scholz, Ulrich; Xiao, Qing; Zhu, Zhibin

doi:10.1002/9783527826186.ch10

Cited by 9 publications

(6 citation statements)

References 306 publications

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“…Amines are among the most widely used compounds in the chemical and related industries, [1,2] as pharmacy, [3,4] agrochemistry [5] and rubber manufacturing [6,7] . On the one hand, many amines are toxic compounds and can be uncontrollably released into the environment as a result of the use of a number of dyes [8] and pesticides [9] .…”

Section: Introductionmentioning

confidence: 99%

Thermoreversible Transformations of the Cyanosubstituted 2‐Oxopyrrole Derivative by the Action of Amines for the Creation of Novel High‐Contrast Coloration/Decoloration Systems

Yu. Belikov,

Milovidova,

Yu. Ievlev

2024

ChemistrySelect

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A new efficient approach to the synthesis of intensely colored 2‐(2‐oxo‐3H‐pyrrol‐3‐ylidene)malononitrile (OP) was developed. Using the reaction of OP with amines, a series of previously unknown colorless organic salts – dicyano(2‐oxo‐2,5‐dihydro‐1H‐pyrrol‐3‐yl)methanides were synthesized, bearing in the structure two fragments of same or diverse amines of different nature (covalent and ionic). TGA‐DTA study of the synthesized salts showed a thermal reversibility of their formation. The introduction of violet OP into paper followed by treatment with amine vapors revealed prospects of using such a system for naked‐eye detection of volatile amines. It was also shown that OP‐based rewritable paper can be created, to which a data can be applied by local heating and erased by the action of amine or temperature.

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Section: Introductionmentioning

confidence: 99%

Thermoreversible Transformations of the Cyanosubstituted 2‐Oxopyrrole Derivative by the Action of Amines for the Creation of Novel High‐Contrast Coloration/Decoloration Systems

Yu. Belikov,

Milovidova,

Yu. Ievlev

2024

ChemistrySelect

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“…Arylamines are the important building blocks in synthetic chemistry. [14] The electrosynthesis-driven CÀ C homocoupling, [12b] NÀ S cross-coupling, [4g] and CÀ O/OÀ H crossmetathesis [4h] of arylamines have been previously realized. However, the performances of AC and DC for these reactions were found to be significantly different, but the underlying mechanisms are unclear.…”

Section: Resultsmentioning

confidence: 99%

“…Arylamines are the important building blocks in synthetic chemistry [14] . The electrosynthesis‐driven C−C homo‐coupling, [12b] N−S cross‐coupling, [4g] and C−O/O−H cross‐metathesis [4h] of arylamines have been previously realized.…”

Section: Resultsmentioning

confidence: 99%

Elucidating the Underlying Reactivities of Alternating Current Electrosynthesis by Time‐Resolved Mapping of Short‐Lived Reactive Intermediates

Wan,

Chen,

Dong

et al. 2023

Angew Chem Int Ed

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Alternating current (AC) electrolysis is an emerging field in synthetic chemistry, while its mechanistic studies are challenged by the effective characterization of the elusive intermediate processes. Herein, we develop an operando electrochemical mass spectrometry platform that allows time‐resolved mapping of stepwise electrosynthetic reactive intermediates in both direct current and alternating current modes. By dissecting the key intermediate processes of electrochemical functionalization of arylamines, the unique reactivities of AC electrosynthesis, including minimizing the over‐oxidation/reduction through the inverse process, and enabling effective reaction of short‐lived intermediates generated by oxidation and reduction in paired electrolysis, were evidenced and verified. Notably, the controlled kinetics of reactive N‐centered radical intermediates in multi‐step sequential AC electrosynthesis to minimize the competing reactions was discovered. Overall, this work provides direct evidence for the mechanism of AC electrolysis, and clarifies the underlying reasons for its high efficiency, which will benefit the rational design of AC electrosynthetic reactions.

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“…1) published their pioneering work on C-N coupling using stoichiometric or even catalytic amounts of copper at elevated temperatures (>200 °C). 4,[10][11][12][13] In this context, the Cu-catalyzed Chan-Lam [14][15][16] and Pd-catalyzed Buchwald-Hartwig coupling 17,18 (Fig. 1) were well adopted as new methodologies in industry and academia.…”

Section: Introductionmentioning

confidence: 99%

“…1) were well adopted as new methodologies in industry and academia. 13 Despite their versatility, all these approaches need pre-functionalized arenes ( e.g. aryl-boron compounds or aryl halides), which requires additional functionalization steps.…”

Section: Introductionmentioning

confidence: 99%

A direct pathway for the coupling of arenes and alkylamines via a heterogeneous zeolite-based photocatalyst

Lemmens¹,

Janssens²,

Gascón³

et al. 2023

Green Chem.

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Recent Advances in the Synthesis of Arylamines in the Light of Application in Pharmaceutical and Chemical Industry

Cited by 9 publications

References 306 publications

Thermoreversible Transformations of the Cyanosubstituted 2‐Oxopyrrole Derivative by the Action of Amines for the Creation of Novel High‐Contrast Coloration/Decoloration Systems

Thermoreversible Transformations of the Cyanosubstituted 2‐Oxopyrrole Derivative by the Action of Amines for the Creation of Novel High‐Contrast Coloration/Decoloration Systems

Elucidating the Underlying Reactivities of Alternating Current Electrosynthesis by Time‐Resolved Mapping of Short‐Lived Reactive Intermediates

A direct pathway for the coupling of arenes and alkylamines via a heterogeneous zeolite-based photocatalyst

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