The Eschenmoser coupling reaction under continuous-flow conditions
The Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Esch...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2011-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.7.135 |
| _version_ | 1818873980366356480 |
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| author | Sukhdeep Singh J. Michael Köhler Andreas Schober G. Alexander Groß |
| author_facet | Sukhdeep Singh J. Michael Köhler Andreas Schober G. Alexander Groß |
| author_sort | Sukhdeep Singh |
| collection | DOAJ |
| description | The Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Eschenmoser coupling needs prolonged reaction times and elevated temperatures to deliver valuable yields. We have used a flow chemistry system to promote the Eschenmoser coupling under enhanced reaction conditions in order to convert the demanding precursors such as S-alkylated secondary thioamides and thiolactames in an efficient way. Under pressurized reaction conditions at about 220 °C, the desired Eschenmoser coupling products were obtained within 70 s residence time. The reaction kinetics was investigated and 15 examples of different building block combinations are given. |
| first_indexed | 2024-12-19T13:03:19Z |
| format | Article |
| id | doaj.art-8464eb59d0734c318460f240336824eb |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T13:03:19Z |
| publishDate | 2011-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-8464eb59d0734c318460f240336824eb2022-12-21T20:20:10ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-08-01711164117210.3762/bjoc.7.1351860-5397-7-135The Eschenmoser coupling reaction under continuous-flow conditionsSukhdeep Singh0J. Michael Köhler1Andreas Schober2G. Alexander Groß3Institute for Chemistry and Biotechnology, Technische Universität Ilmenau, Weimarerstr. 32, D-98693-IlmenauInstitute for Chemistry and Biotechnology, Technische Universität Ilmenau, Weimarerstr. 32, D-98693-IlmenauInstitute for Chemistry and Biotechnology, Technische Universität Ilmenau, Weimarerstr. 32, D-98693-IlmenauInstitute for Chemistry and Biotechnology, Technische Universität Ilmenau, Weimarerstr. 32, D-98693-IlmenauThe Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Eschenmoser coupling needs prolonged reaction times and elevated temperatures to deliver valuable yields. We have used a flow chemistry system to promote the Eschenmoser coupling under enhanced reaction conditions in order to convert the demanding precursors such as S-alkylated secondary thioamides and thiolactames in an efficient way. Under pressurized reaction conditions at about 220 °C, the desired Eschenmoser coupling products were obtained within 70 s residence time. The reaction kinetics was investigated and 15 examples of different building block combinations are given.https://doi.org/10.3762/bjoc.7.135activation energyepisulfideflow chemistryketo iminekineticsS-alkylationsulfide contractiontriisopropyl phosphite |
| spellingShingle | Sukhdeep Singh J. Michael Köhler Andreas Schober G. Alexander Groß The Eschenmoser coupling reaction under continuous-flow conditions Beilstein Journal of Organic Chemistry activation energy episulfide flow chemistry keto imine kinetics S-alkylation sulfide contraction triisopropyl phosphite |
| title | The Eschenmoser coupling reaction under continuous-flow conditions |
| title_full | The Eschenmoser coupling reaction under continuous-flow conditions |
| title_fullStr | The Eschenmoser coupling reaction under continuous-flow conditions |
| title_full_unstemmed | The Eschenmoser coupling reaction under continuous-flow conditions |
| title_short | The Eschenmoser coupling reaction under continuous-flow conditions |
| title_sort | eschenmoser coupling reaction under continuous flow conditions |
| topic | activation energy episulfide flow chemistry keto imine kinetics S-alkylation sulfide contraction triisopropyl phosphite |
| url | https://doi.org/10.3762/bjoc.7.135 |
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