BrCF2CN for photocatalytic cyanodifluoromethylation
Abstract Considering the unique electronic properties of the CF2 and the CN groups, the CF2CN group has significant potential in drug and agrochemical development, as well as material sciences. However, incorporating a CF2CN group remains a considerable challenge. In this work, we disclose a use of...
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55797-4 |
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| _version_ | 1841544444047785984 |
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| author | Xin-Jun Yang Jin-Hong Lin Ji-Chang Xiao |
| author_facet | Xin-Jun Yang Jin-Hong Lin Ji-Chang Xiao |
| author_sort | Xin-Jun Yang |
| collection | DOAJ |
| description | Abstract Considering the unique electronic properties of the CF2 and the CN groups, the CF2CN group has significant potential in drug and agrochemical development, as well as material sciences. However, incorporating a CF2CN group remains a considerable challenge. In this work, we disclose a use of bromodifluoroacetonitrile (BrCF2CN), a cost-effective and readily available reagent, as a radical source for cyanodifluoromethylation of alkyl alkenes, aryl alkenes, alkynes, and (hetero)arenes under photocatalytic conditions. This protocol demonstrates an exceptionally broad substrate scope and remarkable tolerance to various functional groups. Notably, the cyanodifluoromethylation of alkynes predominantly provides sterically hindered alkenes, a thermodynamically unfavorable outcome, and (hetero)arene C-H bonds are directly amenable to cyanodifluoromethylation without pre-functionalization. |
| format | Article |
| id | doaj-art-80974b906d364805bec4f04603e3c692 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-80974b906d364805bec4f04603e3c6922025-01-12T12:30:53ZengNature PortfolioNature Communications2041-17232025-01-0116111110.1038/s41467-024-55797-4BrCF2CN for photocatalytic cyanodifluoromethylationXin-Jun Yang0Jin-Hong Lin1Ji-Chang Xiao2Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesKey Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesKey Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesAbstract Considering the unique electronic properties of the CF2 and the CN groups, the CF2CN group has significant potential in drug and agrochemical development, as well as material sciences. However, incorporating a CF2CN group remains a considerable challenge. In this work, we disclose a use of bromodifluoroacetonitrile (BrCF2CN), a cost-effective and readily available reagent, as a radical source for cyanodifluoromethylation of alkyl alkenes, aryl alkenes, alkynes, and (hetero)arenes under photocatalytic conditions. This protocol demonstrates an exceptionally broad substrate scope and remarkable tolerance to various functional groups. Notably, the cyanodifluoromethylation of alkynes predominantly provides sterically hindered alkenes, a thermodynamically unfavorable outcome, and (hetero)arene C-H bonds are directly amenable to cyanodifluoromethylation without pre-functionalization.https://doi.org/10.1038/s41467-024-55797-4 |
| spellingShingle | Xin-Jun Yang Jin-Hong Lin Ji-Chang Xiao BrCF2CN for photocatalytic cyanodifluoromethylation Nature Communications |
| title | BrCF2CN for photocatalytic cyanodifluoromethylation |
| title_full | BrCF2CN for photocatalytic cyanodifluoromethylation |
| title_fullStr | BrCF2CN for photocatalytic cyanodifluoromethylation |
| title_full_unstemmed | BrCF2CN for photocatalytic cyanodifluoromethylation |
| title_short | BrCF2CN for photocatalytic cyanodifluoromethylation |
| title_sort | brcf2cn for photocatalytic cyanodifluoromethylation |
| url | https://doi.org/10.1038/s41467-024-55797-4 |
| work_keys_str_mv | AT xinjunyang brcf2cnforphotocatalyticcyanodifluoromethylation AT jinhonglin brcf2cnforphotocatalyticcyanodifluoromethylation AT jichangxiao brcf2cnforphotocatalyticcyanodifluoromethylation |