Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst
3-Alkenylindoles are biologically and medicinally very important compounds, and their syntheses have received considerable attention. Herein, we report the synthesis of 3-alkenylindoles via a regioselective alkenylation of indoles, catalysed by a ruthenium nanocatalyst (RuNC). The reaction tolerates...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2020-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.16.16 |
| _version_ | 1818606290456281088 |
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| author | Abhijit Paul Debnath Chatterjee Srirupa Banerjee Somnath Yadav |
| author_facet | Abhijit Paul Debnath Chatterjee Srirupa Banerjee Somnath Yadav |
| author_sort | Abhijit Paul |
| collection | DOAJ |
| description | 3-Alkenylindoles are biologically and medicinally very important compounds, and their syntheses have received considerable attention. Herein, we report the synthesis of 3-alkenylindoles via a regioselective alkenylation of indoles, catalysed by a ruthenium nanocatalyst (RuNC). The reaction tolerates several electron-withdrawing and electron-donating groups on the indole moiety. Additionally, a “robustness screen” has also been employed to demonstrate the tolerance of several functional groups relevant to medicinal chemistry. With respect to the Ru nanocatalyst, it has been demonstrated that it is recoverable and recyclable up to four cycles. Also, the catalyst acts through a heterogeneous mechanism, which has been proven by various techniques, such as ICPMS and three-phase tests. The nature of the Ru nanocatalyst surface has also been thoroughly examined by various techniques, and it has been found that the oxides on the surface are responsible for the high catalytic efficiency of the Ru nanocatalyst. |
| first_indexed | 2024-12-16T14:08:30Z |
| format | Article |
| id | doaj.art-1003d4eadf184dda958589e7aeb27e90 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T14:08:30Z |
| publishDate | 2020-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-1003d4eadf184dda958589e7aeb27e902022-12-21T22:28:51ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-01-0116114014810.3762/bjoc.16.161860-5397-16-16Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalystAbhijit Paul0Debnath Chatterjee1Srirupa Banerjee2Somnath Yadav3Department of Chemistry, Indian Institute of Technology (ISM), Dhanbad, 826004, Jharkhand, IndiaDepartment of Chemistry, Indian Institute of Technology (ISM), Dhanbad, 826004, Jharkhand, IndiaDepartment of Chemistry, Bethune College, Bidhan Sarani, Kolkata, 700006, West Bengal, IndiaDepartment of Chemistry, Indian Institute of Technology (ISM), Dhanbad, 826004, Jharkhand, India3-Alkenylindoles are biologically and medicinally very important compounds, and their syntheses have received considerable attention. Herein, we report the synthesis of 3-alkenylindoles via a regioselective alkenylation of indoles, catalysed by a ruthenium nanocatalyst (RuNC). The reaction tolerates several electron-withdrawing and electron-donating groups on the indole moiety. Additionally, a “robustness screen” has also been employed to demonstrate the tolerance of several functional groups relevant to medicinal chemistry. With respect to the Ru nanocatalyst, it has been demonstrated that it is recoverable and recyclable up to four cycles. Also, the catalyst acts through a heterogeneous mechanism, which has been proven by various techniques, such as ICPMS and three-phase tests. The nature of the Ru nanocatalyst surface has also been thoroughly examined by various techniques, and it has been found that the oxides on the surface are responsible for the high catalytic efficiency of the Ru nanocatalyst.https://doi.org/10.3762/bjoc.16.16alkenylationc–h activationheterogeneous catalysisnanocatalysisruthenium catalysis |
| spellingShingle | Abhijit Paul Debnath Chatterjee Srirupa Banerjee Somnath Yadav Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst Beilstein Journal of Organic Chemistry alkenylation c–h activation heterogeneous catalysis nanocatalysis ruthenium catalysis |
| title | Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst |
| title_full | Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst |
| title_fullStr | Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst |
| title_full_unstemmed | Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst |
| title_short | Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst |
| title_sort | synthesis of 3 alkenylindoles through regioselective c h alkenylation of indoles by a ruthenium nanocatalyst |
| topic | alkenylation c–h activation heterogeneous catalysis nanocatalysis ruthenium catalysis |
| url | https://doi.org/10.3762/bjoc.16.16 |
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