Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a base
Iodine-promoted dimerization of enolates of methyl 2-arylacetates generated with tBuOK under equilibrium conditions are reported. The oxidative homocoupling reaction furnishes a mixture of dl and meso dimers in moderate to good yields and diastereoselectivity. Electron-withdrawing substituents on th...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-01-01
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| Series: | Results in Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715622001266 |
| _version_ | 1811294674784092160 |
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| author | Ahmed Y. Nuriye Joseph Barr |
| author_facet | Ahmed Y. Nuriye Joseph Barr |
| author_sort | Ahmed Y. Nuriye |
| collection | DOAJ |
| description | Iodine-promoted dimerization of enolates of methyl 2-arylacetates generated with tBuOK under equilibrium conditions are reported. The oxidative homocoupling reaction furnishes a mixture of dl and meso dimers in moderate to good yields and diastereoselectivity. Electron-withdrawing substituents on the aryl ring seem to facilitate dimerization leading to higher yields and ortho-substituted aryl acetates afford better diastereoselectivity. |
| first_indexed | 2024-04-13T05:20:57Z |
| format | Article |
| id | doaj.art-3dde626fc2d5457b8bc6ab8aea4ca841 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-04-13T05:20:57Z |
| publishDate | 2022-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-3dde626fc2d5457b8bc6ab8aea4ca8412022-12-22T03:00:45ZengElsevierResults in Chemistry2211-71562022-01-014100407Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a baseAhmed Y. Nuriye0Joseph Barr1Corresponding author.; Department of Chemistry, The Pennsylvania State University, Abington College, 1600 Woodland Road, Abington, PA 19001, United StatesDepartment of Chemistry, The Pennsylvania State University, Abington College, 1600 Woodland Road, Abington, PA 19001, United StatesIodine-promoted dimerization of enolates of methyl 2-arylacetates generated with tBuOK under equilibrium conditions are reported. The oxidative homocoupling reaction furnishes a mixture of dl and meso dimers in moderate to good yields and diastereoselectivity. Electron-withdrawing substituents on the aryl ring seem to facilitate dimerization leading to higher yields and ortho-substituted aryl acetates afford better diastereoselectivity.http://www.sciencedirect.com/science/article/pii/S2211715622001266Oxidative homocouplingEnolate chemistryDiarylsuccinatePotassium tert-butoxide |
| spellingShingle | Ahmed Y. Nuriye Joseph Barr Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a base Results in Chemistry Oxidative homocoupling Enolate chemistry Diarylsuccinate Potassium tert-butoxide |
| title | Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a base |
| title_full | Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a base |
| title_fullStr | Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a base |
| title_full_unstemmed | Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a base |
| title_short | Iodine-promoted oxidative homocoupling of methyl 2-arylacetates under equilibrium conditions using potassium tert-butoxide as a base |
| title_sort | iodine promoted oxidative homocoupling of methyl 2 arylacetates under equilibrium conditions using potassium tert butoxide as a base |
| topic | Oxidative homocoupling Enolate chemistry Diarylsuccinate Potassium tert-butoxide |
| url | http://www.sciencedirect.com/science/article/pii/S2211715622001266 |
| work_keys_str_mv | AT ahmedynuriye iodinepromotedoxidativehomocouplingofmethyl2arylacetatesunderequilibriumconditionsusingpotassiumtertbutoxideasabase AT josephbarr iodinepromotedoxidativehomocouplingofmethyl2arylacetatesunderequilibriumconditionsusingpotassiumtertbutoxideasabase |