Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework
Cloke-Wilson rearrangement has been well studied, in which cyclopropyl ketones or cyclopropyl imines could be transformed to dihydrofuran or dihydropyrrole derivatives through a tandem ring-opening/recyclization process. Herein, we report a new version of Cloke-Wilson rearrangement, in which the rin...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-03-01
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| Series: | Tetrahedron Chem |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666951X21000012 |
| _version_ | 1827854843319943168 |
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| author | Zhen Liu Yin Wei Min Shi |
| author_facet | Zhen Liu Yin Wei Min Shi |
| author_sort | Zhen Liu |
| collection | DOAJ |
| description | Cloke-Wilson rearrangement has been well studied, in which cyclopropyl ketones or cyclopropyl imines could be transformed to dihydrofuran or dihydropyrrole derivatives through a tandem ring-opening/recyclization process. Herein, we report a new version of Cloke-Wilson rearrangement, in which the ring-opening/recyclization of cyclopropyl ketones upon visible-light-induced photoredox catalysis can provide oxy-bridged macrocyclic frameworks under mild reaction conditions, and the reagent XRf plays dual roles in the catalytic cycle. The reaction proceeds through a ring-opening and an interrupted recyclization by intramolecular nucleophilic attack with the in situ generated radical cation. The reaction mechanism was proposed on the basis of control, deuterium labeling, Stern–Volmer quenching and CV measuring experiments. This protocol can afford a series of oxy-bridged macrocyclic frameworks with broad substrate scope and good functional-group tolerance. In addition, a variety of 2,2-disubstituted oxy-bridged macrocyclic indolinones can be obtained efficiently by simple manipulation from the products. |
| first_indexed | 2024-03-12T11:35:55Z |
| format | Article |
| id | doaj.art-d4dc657e6ea048a49eeaf4b545d7cf86 |
| institution | Directory Open Access Journal |
| issn | 2666-951X |
| language | English |
| last_indexed | 2024-03-12T11:35:55Z |
| publishDate | 2022-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Tetrahedron Chem |
| spelling | doaj.art-d4dc657e6ea048a49eeaf4b545d7cf862023-09-01T05:03:16ZengElsevierTetrahedron Chem2666-951X2022-03-011100001Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic frameworkZhen Liu0Yin Wei1Min Shi2Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Meilong Road No.130, Shanghai, 200237, ChinaState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China; Corresponding author.Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Meilong Road No.130, Shanghai, 200237, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China; Corresponding author. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Meilong Road No.130, Shanghai, 200237, China.Cloke-Wilson rearrangement has been well studied, in which cyclopropyl ketones or cyclopropyl imines could be transformed to dihydrofuran or dihydropyrrole derivatives through a tandem ring-opening/recyclization process. Herein, we report a new version of Cloke-Wilson rearrangement, in which the ring-opening/recyclization of cyclopropyl ketones upon visible-light-induced photoredox catalysis can provide oxy-bridged macrocyclic frameworks under mild reaction conditions, and the reagent XRf plays dual roles in the catalytic cycle. The reaction proceeds through a ring-opening and an interrupted recyclization by intramolecular nucleophilic attack with the in situ generated radical cation. The reaction mechanism was proposed on the basis of control, deuterium labeling, Stern–Volmer quenching and CV measuring experiments. This protocol can afford a series of oxy-bridged macrocyclic frameworks with broad substrate scope and good functional-group tolerance. In addition, a variety of 2,2-disubstituted oxy-bridged macrocyclic indolinones can be obtained efficiently by simple manipulation from the products.http://www.sciencedirect.com/science/article/pii/S2666951X21000012Cyclopropyl ketonesVisible-light-inducedInterrupted Cloke−Wilson rearrangementOxy-bridged macrocycleIndolinones |
| spellingShingle | Zhen Liu Yin Wei Min Shi Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework Tetrahedron Chem Cyclopropyl ketones Visible-light-induced Interrupted Cloke−Wilson rearrangement Oxy-bridged macrocycle Indolinones |
| title | Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework |
| title_full | Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework |
| title_fullStr | Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework |
| title_full_unstemmed | Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework |
| title_short | Visible-light-mediated interrupted Cloke-Wilson rearrangement of cyclopropyl ketones to construct oxy-bridged macrocyclic framework |
| title_sort | visible light mediated interrupted cloke wilson rearrangement of cyclopropyl ketones to construct oxy bridged macrocyclic framework |
| topic | Cyclopropyl ketones Visible-light-induced Interrupted Cloke−Wilson rearrangement Oxy-bridged macrocycle Indolinones |
| url | http://www.sciencedirect.com/science/article/pii/S2666951X21000012 |
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