A Photochemical Intramolecular C-N Coupling Toward the Synthesis of Benzimidazole-Fused Phenanthridines.
| Autor: | Bera SK; School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar, PO Bhimpur-Padanpur, District Khurda, Jatni, Odisha 752050, India., Boruah PJ; Department of Chemistry, National Institute of Technology Meghalaya, Shillong 793003, Meghalaya, India., Parida SS; School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar, PO Bhimpur-Padanpur, District Khurda, Jatni, Odisha 752050, India., Paul AK; Department of Chemistry, National Institute of Technology Meghalaya, Shillong 793003, Meghalaya, India., Mal P; School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar, PO Bhimpur-Padanpur, District Khurda, Jatni, Odisha 752050, India. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2021 Jul 16; Vol. 86 (14), pp. 9587-9602. Date of Electronic Publication: 2021 Jun 30. |
| DOI: | 10.1021/acs.joc.1c00871 |
| Abstrakt: | Herein, we report a direct photochemical dehydrogenative C-N coupling of unactivated C(sp 2 )-H and N(sp 2 )-H bonds. The catalysts or additive-free transformation of 2-([1,1'-biphenyl]-2-yl)-1 H -benzo[ d ]imidazole to benzo[4,5]imidazo[1,2- f ]phenanthridine was achieved at ∼350 nm of irradiation via ε-hydrogen abstraction. DFT calculations helped to understand that the N-H···π interaction was essential for the reaction to proceed at a lower energy than expected. |
| Databáze: | MEDLINE |
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