Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives
An efficient entry to the preparation of elusive 4-unsubstituted-3-iodo-2H-chromenes has been accomplished as result of a catalytic cyclization. Thus, upon exposition of [(3-iodoprop-2-yn-1-yl)oxy]arenes to IPrAuNTf2 (3 mol %), in 1,4-dioxane at 100 °C, the desired heterocyclic motif is readily asse...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2013-10-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.249 |
| _version_ | 1818445089611972608 |
|---|---|
| author | Pablo Morán-Poladura Eduardo Rubio José M. González |
| author_facet | Pablo Morán-Poladura Eduardo Rubio José M. González |
| author_sort | Pablo Morán-Poladura |
| collection | DOAJ |
| description | An efficient entry to the preparation of elusive 4-unsubstituted-3-iodo-2H-chromenes has been accomplished as result of a catalytic cyclization. Thus, upon exposition of [(3-iodoprop-2-yn-1-yl)oxy]arenes to IPrAuNTf2 (3 mol %), in 1,4-dioxane at 100 °C, the desired heterocyclic motif is readily assembled. This process nicely tolerates a variety of functional groups and, interestingly, it is compatible with the presence of strong electron-withdrawing groups attached to the arene. The overall transformation can be termed as a new example of a migratory cycloisomerization and, formally, it involves well-blended 1,2-iodine shift and hydroarylation steps. |
| first_indexed | 2024-12-14T19:26:17Z |
| format | Article |
| id | doaj.art-30fd91ca7b6f446fb8f9c452afe2d692 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T19:26:17Z |
| publishDate | 2013-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-30fd91ca7b6f446fb8f9c452afe2d6922022-12-21T22:50:12ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-10-01912120212810.3762/bjoc.9.2491860-5397-9-249Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivativesPablo Morán-Poladura0Eduardo Rubio1José M. González2Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, C/Julián Clavería 8, Oviedo, 33006, SpainDepartamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, C/Julián Clavería 8, Oviedo, 33006, SpainDepartamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, C/Julián Clavería 8, Oviedo, 33006, SpainAn efficient entry to the preparation of elusive 4-unsubstituted-3-iodo-2H-chromenes has been accomplished as result of a catalytic cyclization. Thus, upon exposition of [(3-iodoprop-2-yn-1-yl)oxy]arenes to IPrAuNTf2 (3 mol %), in 1,4-dioxane at 100 °C, the desired heterocyclic motif is readily assembled. This process nicely tolerates a variety of functional groups and, interestingly, it is compatible with the presence of strong electron-withdrawing groups attached to the arene. The overall transformation can be termed as a new example of a migratory cycloisomerization and, formally, it involves well-blended 1,2-iodine shift and hydroarylation steps.https://doi.org/10.3762/bjoc.9.249alkynechromenegoldgold catalysishydroarylationiodine |
| spellingShingle | Pablo Morán-Poladura Eduardo Rubio José M. González Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives Beilstein Journal of Organic Chemistry alkyne chromene gold gold catalysis hydroarylation iodine |
| title | Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives |
| title_full | Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives |
| title_fullStr | Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives |
| title_full_unstemmed | Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives |
| title_short | Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives |
| title_sort | gold i catalyzed hydroarylation reaction of aryl 3 iodoprop 2 yn 1 yl ethers synthesis of 3 iodo 2h chromene derivatives |
| topic | alkyne chromene gold gold catalysis hydroarylation iodine |
| url | https://doi.org/10.3762/bjoc.9.249 |
| work_keys_str_mv | AT pablomoranpoladura goldicatalyzedhydroarylationreactionofaryl3iodoprop2yn1yletherssynthesisof3iodo2hchromenederivatives AT eduardorubio goldicatalyzedhydroarylationreactionofaryl3iodoprop2yn1yletherssynthesisof3iodo2hchromenederivatives AT josemgonzalez goldicatalyzedhydroarylationreactionofaryl3iodoprop2yn1yletherssynthesisof3iodo2hchromenederivatives |