Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides
Isocyanides insertions represent an important transformation in the palladium-catalyzed reactions landscape. However, one of their most significant limitations is in the use of inactivated alkyl electrophiles. Palladium photocatalysis has been proven as a solid tool for the generation of alkyl radic...
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2025-06-01
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| author | Andrea Messina Filippo Monticelli Tiziano Miroglio Anna Gagliardi Igor Viviani Luca Banfi Renata Riva Lisa Moni Andrea Basso Chiara Lambruschini |
| author_facet | Andrea Messina Filippo Monticelli Tiziano Miroglio Anna Gagliardi Igor Viviani Luca Banfi Renata Riva Lisa Moni Andrea Basso Chiara Lambruschini |
| author_sort | Andrea Messina |
| collection | DOAJ |
| description | Isocyanides insertions represent an important transformation in the palladium-catalyzed reactions landscape. However, one of their most significant limitations is in the use of inactivated alkyl electrophiles. Palladium photocatalysis has been proven as a solid tool for the generation of alkyl radicals from alkyl halides, which may engage in subsequent transformations with a variety of reaction partners, closing the catalytic cycle. Herein, we report the mild three-component isocyanide insertions into inactivated alkyl iodides mediated by the catalytic activity of a photoexcited palladium complex. We investigated the scope of the reaction obtaining differently substituted secondary amides in good to high yields. We also investigated the mechanism, hypothesizing a key role of 4-(<i>N</i>,<i>N</i>-dimethylamino)pyridine in the outcome of the reaction. |
| format | Article |
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| issn | 1420-3049 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-4b2994ca8f5b455f86f7059a2f0a66b42025-06-25T14:13:37ZengMDPI AGMolecules1420-30492025-06-013012258410.3390/molecules30122584Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl IodidesAndrea Messina0Filippo Monticelli1Tiziano Miroglio2Anna Gagliardi3Igor Viviani4Luca Banfi5Renata Riva6Lisa Moni7Andrea Basso8Chiara Lambruschini9Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, ItalyIsocyanides insertions represent an important transformation in the palladium-catalyzed reactions landscape. However, one of their most significant limitations is in the use of inactivated alkyl electrophiles. Palladium photocatalysis has been proven as a solid tool for the generation of alkyl radicals from alkyl halides, which may engage in subsequent transformations with a variety of reaction partners, closing the catalytic cycle. Herein, we report the mild three-component isocyanide insertions into inactivated alkyl iodides mediated by the catalytic activity of a photoexcited palladium complex. We investigated the scope of the reaction obtaining differently substituted secondary amides in good to high yields. We also investigated the mechanism, hypothesizing a key role of 4-(<i>N</i>,<i>N</i>-dimethylamino)pyridine in the outcome of the reaction.https://www.mdpi.com/1420-3049/30/12/2584isocyanide insertionradical additionpalladium catalysisphotocatalysismulticomponent reactionsamide synthesis |
| spellingShingle | Andrea Messina Filippo Monticelli Tiziano Miroglio Anna Gagliardi Igor Viviani Luca Banfi Renata Riva Lisa Moni Andrea Basso Chiara Lambruschini Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides Molecules isocyanide insertion radical addition palladium catalysis photocatalysis multicomponent reactions amide synthesis |
| title | Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides |
| title_full | Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides |
| title_fullStr | Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides |
| title_full_unstemmed | Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides |
| title_short | Photoexcited Palladium Complex-Catalyzed Isocyanide Insertion into Inactivated Alkyl Iodides |
| title_sort | photoexcited palladium complex catalyzed isocyanide insertion into inactivated alkyl iodides |
| topic | isocyanide insertion radical addition palladium catalysis photocatalysis multicomponent reactions amide synthesis |
| url | https://www.mdpi.com/1420-3049/30/12/2584 |
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