C–H Trifluoromethylthiolation of aldehyde hydrazones
The selective C–H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C–SCF3 bond was achieved under oxidative and...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2024-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.242 |
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| author | Victor Levet Balu Ramesh Congyang Wang Tatiana Besset |
| author_facet | Victor Levet Balu Ramesh Congyang Wang Tatiana Besset |
| author_sort | Victor Levet |
| collection | DOAJ |
| description | The selective C–H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C–SCF3 bond was achieved under oxidative and mild reaction conditions in the presence of the readily available AgSCF3 salt via a one-pot sequential process (28 examples, up to 91% yield). Mechanistic investigations revealed that AgSCF3 was the active species in the transformation. |
| format | Article |
| id | doaj-art-d9d2c43c610f4bf5afeadc26d0bdbe23 |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-d9d2c43c610f4bf5afeadc26d0bdbe232025-08-20T02:18:24ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-11-012012883289010.3762/bjoc.20.2421860-5397-20-242C–H Trifluoromethylthiolation of aldehyde hydrazonesVictor Levet0Balu Ramesh1Congyang Wang2Tatiana Besset3INSA Rouen Normandie, Univ Rouen Normandie, CNRS, Normandie Univ, COBRA UMR 6014, INC3M FR 3038, F-76000 Rouen, France INSA Rouen Normandie, Univ Rouen Normandie, CNRS, Normandie Univ, COBRA UMR 6014, INC3M FR 3038, F-76000 Rouen, France Beijing National Laboratory for Molecular Sciences CAS key Laboratory of Molecular Recognition and Function CAS Research/Education Center for Excellence in Molecular Sciences Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China INSA Rouen Normandie, Univ Rouen Normandie, CNRS, Normandie Univ, COBRA UMR 6014, INC3M FR 3038, F-76000 Rouen, France The selective C–H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C–SCF3 bond was achieved under oxidative and mild reaction conditions in the presence of the readily available AgSCF3 salt via a one-pot sequential process (28 examples, up to 91% yield). Mechanistic investigations revealed that AgSCF3 was the active species in the transformation.https://doi.org/10.3762/bjoc.20.242c–h bond functionalizationc–s bond formationhydrazonessynthetic methodtrifluoromethylthiolation |
| spellingShingle | Victor Levet Balu Ramesh Congyang Wang Tatiana Besset C–H Trifluoromethylthiolation of aldehyde hydrazones Beilstein Journal of Organic Chemistry c–h bond functionalization c–s bond formation hydrazones synthetic method trifluoromethylthiolation |
| title | C–H Trifluoromethylthiolation of aldehyde hydrazones |
| title_full | C–H Trifluoromethylthiolation of aldehyde hydrazones |
| title_fullStr | C–H Trifluoromethylthiolation of aldehyde hydrazones |
| title_full_unstemmed | C–H Trifluoromethylthiolation of aldehyde hydrazones |
| title_short | C–H Trifluoromethylthiolation of aldehyde hydrazones |
| title_sort | c h trifluoromethylthiolation of aldehyde hydrazones |
| topic | c–h bond functionalization c–s bond formation hydrazones synthetic method trifluoromethylthiolation |
| url | https://doi.org/10.3762/bjoc.20.242 |
| work_keys_str_mv | AT victorlevet chtrifluoromethylthiolationofaldehydehydrazones AT baluramesh chtrifluoromethylthiolationofaldehydehydrazones AT congyangwang chtrifluoromethylthiolationofaldehydehydrazones AT tatianabesset chtrifluoromethylthiolationofaldehydehydrazones |