Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles
The importance of functionalized imidazo heterocycles has often been featured in several impactful research both from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay C–H functionalization enabled by organophotocatalysis starring zinc acet...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.19.48 |
| _version_ | 1797809594955726848 |
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| author | Deepak Singh Shyamal Pramanik Soumitra Maity |
| author_facet | Deepak Singh Shyamal Pramanik Soumitra Maity |
| author_sort | Deepak Singh |
| collection | DOAJ |
| description | The importance of functionalized imidazo heterocycles has often been featured in several impactful research both from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay C–H functionalization enabled by organophotocatalysis starring zinc acetate in the triple role of an activator, ion scavenger as well as an acetylating reagent. The mechanistic investigation revealed a sequential sp2 and sp3 C–H activation, followed by functionalization driven by zinc acetate coupled with the photocatalyst PTH. A variety of imidazo[1,2-a]pyridines and related heterocycles were explored as substrates along with several active methylene reagents, all generating the products with excellent yields and regioselectivity, thus confirming excellent functional group tolerability. |
| first_indexed | 2024-03-13T06:55:05Z |
| format | Article |
| id | doaj.art-a92aaeb6ec6241f09e6410e48aafc586 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-03-13T06:55:05Z |
| publishDate | 2023-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-a92aaeb6ec6241f09e6410e48aafc5862023-06-07T12:01:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-05-0119166667310.3762/bjoc.19.481860-5397-19-48Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocyclesDeepak Singh0Shyamal Pramanik1Soumitra Maity2Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, JH 826004, India Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, JH 826004, India Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, JH 826004, India The importance of functionalized imidazo heterocycles has often been featured in several impactful research both from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay C–H functionalization enabled by organophotocatalysis starring zinc acetate in the triple role of an activator, ion scavenger as well as an acetylating reagent. The mechanistic investigation revealed a sequential sp2 and sp3 C–H activation, followed by functionalization driven by zinc acetate coupled with the photocatalyst PTH. A variety of imidazo[1,2-a]pyridines and related heterocycles were explored as substrates along with several active methylene reagents, all generating the products with excellent yields and regioselectivity, thus confirming excellent functional group tolerability.https://doi.org/10.3762/bjoc.19.48c–h functionalizationimidazo heterocyclesphotoredoxregioselectiverelay catalysis |
| spellingShingle | Deepak Singh Shyamal Pramanik Soumitra Maity Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles Beilstein Journal of Organic Chemistry c–h functionalization imidazo heterocycles photoredox regioselective relay catalysis |
| title | Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles |
| title_full | Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles |
| title_fullStr | Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles |
| title_full_unstemmed | Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles |
| title_short | Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles |
| title_sort | photocatalytic sequential c h functionalization expediting acetoxymalonylation of imidazo heterocycles |
| topic | c–h functionalization imidazo heterocycles photoredox regioselective relay catalysis |
| url | https://doi.org/10.3762/bjoc.19.48 |
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