CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands
A protocol has been developed to prepare 1,2-allenyl ketones using molecular oxygen in air or pure oxygen as the oxidant from 2,3-allenylic alcohols with moderate to good yields under mild conditions. In this reaction CuCl (20 mol %) with 1,10-phenanthroline (10 mol %) and bipyridine (10 mol %) was...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2011-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.7.51 |
| _version_ | 1818852980476084224 |
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| author | Shuxu Gao Yu Liu Shengming Ma |
| author_facet | Shuxu Gao Yu Liu Shengming Ma |
| author_sort | Shuxu Gao |
| collection | DOAJ |
| description | A protocol has been developed to prepare 1,2-allenyl ketones using molecular oxygen in air or pure oxygen as the oxidant from 2,3-allenylic alcohols with moderate to good yields under mild conditions. In this reaction CuCl (20 mol %) with 1,10-phenanthroline (10 mol %) and bipyridine (10 mol %) was used as the catalyst. It is interesting to observe that the use of the mixed ligands is important for the higher yields of this transformation: With the monoligand approach developed by Markó et al., the yields are relatively lower. |
| first_indexed | 2024-12-19T07:29:32Z |
| format | Article |
| id | doaj.art-0446e51d9c1a498ea0f0565eb07c093f |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T07:29:32Z |
| publishDate | 2011-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-0446e51d9c1a498ea0f0565eb07c093f2022-12-21T20:30:44ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-04-017139640310.3762/bjoc.7.511860-5397-7-51CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligandsShuxu Gao0Yu Liu1Shengming Ma2Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. ChinaShanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. ChinaShanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. ChinaA protocol has been developed to prepare 1,2-allenyl ketones using molecular oxygen in air or pure oxygen as the oxidant from 2,3-allenylic alcohols with moderate to good yields under mild conditions. In this reaction CuCl (20 mol %) with 1,10-phenanthroline (10 mol %) and bipyridine (10 mol %) was used as the catalyst. It is interesting to observe that the use of the mixed ligands is important for the higher yields of this transformation: With the monoligand approach developed by Markó et al., the yields are relatively lower.https://doi.org/10.3762/bjoc.7.51allenic ketoneallenolCu(I) catalystoxidation |
| spellingShingle | Shuxu Gao Yu Liu Shengming Ma CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands Beilstein Journal of Organic Chemistry allenic ketone allenol Cu(I) catalyst oxidation |
| title | CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands |
| title_full | CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands |
| title_fullStr | CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands |
| title_full_unstemmed | CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands |
| title_short | CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands |
| title_sort | cucl catalyzed aerobic oxidation of 2 3 allenols to 1 2 allenic ketones with 1 1 combination of phenanthroline and bipyridine as ligands |
| topic | allenic ketone allenol Cu(I) catalyst oxidation |
| url | https://doi.org/10.3762/bjoc.7.51 |
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