Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions
The Morita–Baylis–Hillman (MBH) reaction of secondary $N$-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that...
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| Format: | Article |
| Language: | English |
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Académie des sciences
2021-09-01
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| Series: | Comptes Rendus. Chimie |
| Subjects: | |
| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.117/ |
| _version_ | 1797651424064045056 |
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| author | Yue, Xiaoyang Verrier, Charlie Ahmar, Mohammed Queneau, Yves |
| author_facet | Yue, Xiaoyang Verrier, Charlie Ahmar, Mohammed Queneau, Yves |
| author_sort | Yue, Xiaoyang |
| collection | DOAJ |
| description | The Morita–Baylis–Hillman (MBH) reaction of secondary $N$-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a $1{:}1$ water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary $N$-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions. |
| first_indexed | 2024-03-11T16:14:43Z |
| format | Article |
| id | doaj.art-e4b8481ca604488f8c7974509efaaa11 |
| institution | Directory Open Access Journal |
| issn | 1878-1543 |
| language | English |
| last_indexed | 2024-03-11T16:14:43Z |
| publishDate | 2021-09-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj.art-e4b8481ca604488f8c7974509efaaa112023-10-24T14:22:55ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432021-09-0124231933010.5802/crchim.11710.5802/crchim.117Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactionsYue, Xiaoyang0https://orcid.org/0000-0002-1547-1687Verrier, Charlie1https://orcid.org/0000-0001-5104-2110Ahmar, Mohammed2https://orcid.org/0000-0001-8477-5214Queneau, Yves3https://orcid.org/0000-0003-4052-061XUniv Lyon, INSA Lyon, Université Claude Bernard Lyon 1, CPE Lyon, UMR 5246, CNRS, ICBMS, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, Bât. E. Lederer, 1 rue Victor Grignard F-69622 Villeurbanne, FranceUniv Lyon, INSA Lyon, Université Claude Bernard Lyon 1, CPE Lyon, UMR 5246, CNRS, ICBMS, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, Bât. E. Lederer, 1 rue Victor Grignard F-69622 Villeurbanne, FranceUniv Lyon, INSA Lyon, Université Claude Bernard Lyon 1, CPE Lyon, UMR 5246, CNRS, ICBMS, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, Bât. E. Lederer, 1 rue Victor Grignard F-69622 Villeurbanne, FranceUniv Lyon, INSA Lyon, Université Claude Bernard Lyon 1, CPE Lyon, UMR 5246, CNRS, ICBMS, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, Bât. E. Lederer, 1 rue Victor Grignard F-69622 Villeurbanne, FranceThe Morita–Baylis–Hillman (MBH) reaction of secondary $N$-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a $1{:}1$ water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary $N$-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.117/Morita–Baylis–HillmanAcrylamidesAqueous solventsBiobased solventsFurfuralHMF |
| spellingShingle | Yue, Xiaoyang Verrier, Charlie Ahmar, Mohammed Queneau, Yves Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions Comptes Rendus. Chimie Morita–Baylis–Hillman Acrylamides Aqueous solvents Biobased solvents Furfural HMF |
| title | Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions |
| title_full | Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions |
| title_fullStr | Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions |
| title_full_unstemmed | Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions |
| title_short | Reactivity of secondary $N$-alkyl acrylamides in Morita–Baylis–Hillman reactions |
| title_sort | reactivity of secondary n alkyl acrylamides in morita baylis hillman reactions |
| topic | Morita–Baylis–Hillman Acrylamides Aqueous solvents Biobased solvents Furfural HMF |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.117/ |
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