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Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues.

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Title: Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues.
Authors: Baudelet, Davy1,2,3, Daïch, Adam4 adam.daich@univ-lehavre.fr, Rigo, Benoît1,2, Lipka, Emmanuelle1,3, Gautret, Philippe1,2, Homerin, Germain1,2, Claverie, Christelle2, Rousseau, Jolanta2, Abuhaie, Cristina-Maria1,2,5, Ghinet, Alina1,2,5
Source: Synthesis. 2016, Vol. 48 Issue 14, p2226-2244. 19p.
Subjects: Arylation, Pyrrolidinones, Copper catalysts, Halides, Aryl group
Abstract: The electronic effects governing the N-arylation of pyrroli-done were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp²-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields. [ABSTRACT FROM AUTHOR]
Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 116636728
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
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  Data: Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues.
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  Data: <searchLink fieldCode="AR" term="%22Baudelet%2C+Davy%22">Baudelet, Davy</searchLink><relatesTo>1,2,3</relatesTo><br /><searchLink fieldCode="AR" term="%22Daïch%2C+Adam%22">Daïch, Adam</searchLink><relatesTo>4</relatesTo><i> adam.daich@univ-lehavre.fr</i><br /><searchLink fieldCode="AR" term="%22Rigo%2C+Benoît%22">Rigo, Benoît</searchLink><relatesTo>1,2</relatesTo><br /><searchLink fieldCode="AR" term="%22Lipka%2C+Emmanuelle%22">Lipka, Emmanuelle</searchLink><relatesTo>1,3</relatesTo><br /><searchLink fieldCode="AR" term="%22Gautret%2C+Philippe%22">Gautret, Philippe</searchLink><relatesTo>1,2</relatesTo><br /><searchLink fieldCode="AR" term="%22Homerin%2C+Germain%22">Homerin, Germain</searchLink><relatesTo>1,2</relatesTo><br /><searchLink fieldCode="AR" term="%22Claverie%2C+Christelle%22">Claverie, Christelle</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Rousseau%2C+Jolanta%22">Rousseau, Jolanta</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Abuhaie%2C+Cristina-Maria%22">Abuhaie, Cristina-Maria</searchLink><relatesTo>1,2,5</relatesTo><br /><searchLink fieldCode="AR" term="%22Ghinet%2C+Alina%22">Ghinet, Alina</searchLink><relatesTo>1,2,5</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Synthesis%22">Synthesis</searchLink>. 2016, Vol. 48 Issue 14, p2226-2244. 19p.
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  Data: <searchLink fieldCode="DE" term="%22Arylation%22">Arylation</searchLink><br /><searchLink fieldCode="DE" term="%22Pyrrolidinones%22">Pyrrolidinones</searchLink><br /><searchLink fieldCode="DE" term="%22Copper+catalysts%22">Copper catalysts</searchLink><br /><searchLink fieldCode="DE" term="%22Halides%22">Halides</searchLink><br /><searchLink fieldCode="DE" term="%22Aryl+group%22">Aryl group</searchLink>
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  Data: The electronic effects governing the N-arylation of pyrroli-done were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp²-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1055/s-0035-1561415
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      – SubjectFull: Arylation
        Type: general
      – SubjectFull: Pyrrolidinones
        Type: general
      – SubjectFull: Copper catalysts
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      – SubjectFull: Halides
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      – TitleFull: Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues.
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              Text: 2016
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