NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation
A novel NHC-catalyzed regiodivergent reaction of ynones with trifluoromethyl ketones consisting of Aldol reactions and intermolecular [3 + 2] annulations has been developed. Employing two different NHC catalysts, various tertiary alcohols and dihyrofuranones containing trifluoromethyl can be obtaine...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-08-01
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| Series: | Tetrahedron Chem |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666951X23000104 |
| _version_ | 1827861344091635712 |
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| author | Fangfang Lu Bai Shi Wei Cao Huiping Yin Tianjiao Huang Kai Zhang Changsheng Yao |
| author_facet | Fangfang Lu Bai Shi Wei Cao Huiping Yin Tianjiao Huang Kai Zhang Changsheng Yao |
| author_sort | Fangfang Lu |
| collection | DOAJ |
| description | A novel NHC-catalyzed regiodivergent reaction of ynones with trifluoromethyl ketones consisting of Aldol reactions and intermolecular [3 + 2] annulations has been developed. Employing two different NHC catalysts, various tertiary alcohols and dihyrofuranones containing trifluoromethyl can be obtained in moderate to good yields (35 examples, up to 91% yield). This protocol features mild reaction conditions, high efficiency and broad substrates scope, promoting the development of NHC catalysis and transformations of ynones. |
| first_indexed | 2024-03-12T13:36:28Z |
| format | Article |
| id | doaj.art-878cf0aff566451e9eb54bee4b5a5dbf |
| institution | Directory Open Access Journal |
| issn | 2666-951X |
| language | English |
| last_indexed | 2024-03-12T13:36:28Z |
| publishDate | 2023-08-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Tetrahedron Chem |
| spelling | doaj.art-878cf0aff566451e9eb54bee4b5a5dbf2023-08-24T04:35:44ZengElsevierTetrahedron Chem2666-951X2023-08-017100044NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulationFangfang Lu0Bai Shi1Wei Cao2Huiping Yin3Tianjiao Huang4Kai Zhang5Changsheng Yao6Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, PR ChinaJiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, PR ChinaJiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, PR ChinaJiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, PR ChinaJiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, PR ChinaCorresponding author.; Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, PR ChinaCorresponding author.; Jiangsu Key Lab of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, PR ChinaA novel NHC-catalyzed regiodivergent reaction of ynones with trifluoromethyl ketones consisting of Aldol reactions and intermolecular [3 + 2] annulations has been developed. Employing two different NHC catalysts, various tertiary alcohols and dihyrofuranones containing trifluoromethyl can be obtained in moderate to good yields (35 examples, up to 91% yield). This protocol features mild reaction conditions, high efficiency and broad substrates scope, promoting the development of NHC catalysis and transformations of ynones.http://www.sciencedirect.com/science/article/pii/S2666951X23000104NHC catalysisRegiodivergenceynonesAldol reaction[3+2] annulation |
| spellingShingle | Fangfang Lu Bai Shi Wei Cao Huiping Yin Tianjiao Huang Kai Zhang Changsheng Yao NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation Tetrahedron Chem NHC catalysis Regiodivergence ynones Aldol reaction [3+2] annulation |
| title | NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation |
| title_full | NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation |
| title_fullStr | NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation |
| title_full_unstemmed | NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation |
| title_short | NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation |
| title_sort | nhc catalyzed regiodivergent transformations of ynones with trifluoromethyl ketones aldol reaction or 3 2 annulation |
| topic | NHC catalysis Regiodivergence ynones Aldol reaction [3+2] annulation |
| url | http://www.sciencedirect.com/science/article/pii/S2666951X23000104 |
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