Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes.
Arenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reac...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
American Chemical Society
2014
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| _version_ | 1826286147469312000 |
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| author | Emer, E Twilton, J Tredwell, M Calderwood, S Collier, T Liégault, B Taillefer, M Gouverneur, V |
| author_facet | Emer, E Twilton, J Tredwell, M Calderwood, S Collier, T Liégault, B Taillefer, M Gouverneur, V |
| author_sort | Emer, E |
| collection | OXFORD |
| description | Arenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)arenes with HF, F/Br, F2, CF3H, and CF3SH sources give direct access to a variety of perfluoroalkyl-substituted arenes presenting with incremental fluorine content. The value of this approach is also demonstrated for radiochemistry and positron emission tomography with the [(18)F]-labeling of CF3CHF-, CF3CBrF-, and CF3CF2-arenes from [(18)F]fluoride. |
| first_indexed | 2024-03-07T01:39:28Z |
| format | Journal article |
| id | oxford-uuid:965bac08-0574-4881-868d-65c3f3e17b5f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:39:28Z |
| publishDate | 2014 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:965bac08-0574-4881-868d-65c3f3e17b5f2022-03-26T23:52:19ZDiversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:965bac08-0574-4881-868d-65c3f3e17b5fEnglishSymplectic Elements at OxfordAmerican Chemical Society2014Emer, ETwilton, JTredwell, MCalderwood, SCollier, TLiégault, BTaillefer, MGouverneur, VArenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)arenes with HF, F/Br, F2, CF3H, and CF3SH sources give direct access to a variety of perfluoroalkyl-substituted arenes presenting with incremental fluorine content. The value of this approach is also demonstrated for radiochemistry and positron emission tomography with the [(18)F]-labeling of CF3CHF-, CF3CBrF-, and CF3CF2-arenes from [(18)F]fluoride. |
| spellingShingle | Emer, E Twilton, J Tredwell, M Calderwood, S Collier, T Liégault, B Taillefer, M Gouverneur, V Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes. |
| title | Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes. |
| title_full | Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes. |
| title_fullStr | Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes. |
| title_full_unstemmed | Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes. |
| title_short | Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes. |
| title_sort | diversity oriented approach to cf3chf cf3cfbr cf3cf2 cf3 2ch and cf3 scf3 ch substituted arenes from 1 diazo 2 2 2 trifluoroethyl arenes |
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