Defluorinative functionalization approach led by difluoromethyl anion chemistry
Abstract Organofluorine compounds have greatly benefited the pharmaceutical, agrochemical, and materials sectors. However, they are plagued by concerns associated with Per- and Polyfluoroalkyl Substances. Additionally, the widespread use of the trifluoromethyl group is facing imminent regulatory scr...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-52842-0 |
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| _version_ | 1841544457569173504 |
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| author | Kensuke Muta Kazuhiro Okamoto Hiroki Nakayama Shuto Wada Aiichiro Nagaki |
| author_facet | Kensuke Muta Kazuhiro Okamoto Hiroki Nakayama Shuto Wada Aiichiro Nagaki |
| author_sort | Kensuke Muta |
| collection | DOAJ |
| description | Abstract Organofluorine compounds have greatly benefited the pharmaceutical, agrochemical, and materials sectors. However, they are plagued by concerns associated with Per- and Polyfluoroalkyl Substances. Additionally, the widespread use of the trifluoromethyl group is facing imminent regulatory scrutiny. Defluorinative functionalization, which converts the trifluoromethyl to the difluoromethyl motifs, represents the most efficient synthetic strategy. However, general methods for robust C(sp 3 )–F bond transformations remain elusive due to challenges in selectivity and functional group tolerance. Here, we present a method for C(sp 3 )–F bond defluorinative functionalization of the trifluoromethyl group via difluoromethyl anion in flow. This new approach tames the reactive difluoromethyl anion, enabling diverse functional group transformations. Our methodology offers a versatile platform for drug and agrochemical discovery, overcoming the limitations associated with fluorinated motifs. |
| format | Article |
| id | doaj-art-afd4d15ac8344bfa8b395cc74d17fbe6 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-afd4d15ac8344bfa8b395cc74d17fbe62025-01-12T12:31:26ZengNature PortfolioNature Communications2041-17232025-01-011611910.1038/s41467-024-52842-0Defluorinative functionalization approach led by difluoromethyl anion chemistryKensuke Muta0Kazuhiro Okamoto1Hiroki Nakayama2Shuto Wada3Aiichiro Nagaki4Department of Chemistry, Graduate School of Science, Hokkaido UniversityDepartment of Chemistry, Graduate School of Science, Hokkaido UniversityDepartment of Chemistry, Graduate School of Science, Hokkaido UniversityDepartment of Chemistry, Graduate School of Science, Hokkaido UniversityDepartment of Chemistry, Graduate School of Science, Hokkaido UniversityAbstract Organofluorine compounds have greatly benefited the pharmaceutical, agrochemical, and materials sectors. However, they are plagued by concerns associated with Per- and Polyfluoroalkyl Substances. Additionally, the widespread use of the trifluoromethyl group is facing imminent regulatory scrutiny. Defluorinative functionalization, which converts the trifluoromethyl to the difluoromethyl motifs, represents the most efficient synthetic strategy. However, general methods for robust C(sp 3 )–F bond transformations remain elusive due to challenges in selectivity and functional group tolerance. Here, we present a method for C(sp 3 )–F bond defluorinative functionalization of the trifluoromethyl group via difluoromethyl anion in flow. This new approach tames the reactive difluoromethyl anion, enabling diverse functional group transformations. Our methodology offers a versatile platform for drug and agrochemical discovery, overcoming the limitations associated with fluorinated motifs.https://doi.org/10.1038/s41467-024-52842-0 |
| spellingShingle | Kensuke Muta Kazuhiro Okamoto Hiroki Nakayama Shuto Wada Aiichiro Nagaki Defluorinative functionalization approach led by difluoromethyl anion chemistry Nature Communications |
| title | Defluorinative functionalization approach led by difluoromethyl anion chemistry |
| title_full | Defluorinative functionalization approach led by difluoromethyl anion chemistry |
| title_fullStr | Defluorinative functionalization approach led by difluoromethyl anion chemistry |
| title_full_unstemmed | Defluorinative functionalization approach led by difluoromethyl anion chemistry |
| title_short | Defluorinative functionalization approach led by difluoromethyl anion chemistry |
| title_sort | defluorinative functionalization approach led by difluoromethyl anion chemistry |
| url | https://doi.org/10.1038/s41467-024-52842-0 |
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