Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐Sulfinylimines
Abstract A micro‐flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro‐flow transformation of N‐sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2019-04-01
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| Series: | ChemistryOpen |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/open.201800286 |
| _version_ | 1827892025048956928 |
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| author | Kazuki Hirano Satoshi Gondo Nagender Punna Etsuko Tokunaga Prof. Dr. Norio Shibata |
| author_facet | Kazuki Hirano Satoshi Gondo Nagender Punna Etsuko Tokunaga Prof. Dr. Norio Shibata |
| author_sort | Kazuki Hirano |
| collection | DOAJ |
| description | Abstract A micro‐flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro‐flow transformation of N‐sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro‐flow synthesis, the formal micro‐flow synthesis of Efavirenz is described. |
| first_indexed | 2024-03-12T21:33:40Z |
| format | Article |
| id | doaj.art-901eaff0a57747c08f6458ce71ba573d |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-03-12T21:33:40Z |
| publishDate | 2019-04-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-901eaff0a57747c08f6458ce71ba573d2023-07-27T14:18:23ZengWiley-VCHChemistryOpen2191-13632019-04-018440641010.1002/open.201800286Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐SulfinyliminesKazuki Hirano0Satoshi Gondo1Nagender Punna2Etsuko Tokunaga3Prof. Dr. Norio Shibata4Department of Life Science and Applied Chemistry, Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 JapanDepartment of Life Science and Applied Chemistry, Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 JapanDepartment of Life Science and Applied Chemistry, Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 JapanDepartment of Life Science and Applied Chemistry, Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 JapanDepartment of Life Science and Applied Chemistry, Department of Nanopharmaceutical Sciences Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 JapanAbstract A micro‐flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro‐flow transformation of N‐sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro‐flow synthesis, the formal micro‐flow synthesis of Efavirenz is described.https://doi.org/10.1002/open.201800286flow chemistrytrifluoromethylfluoroformmicro-flowgaseous |
| spellingShingle | Kazuki Hirano Satoshi Gondo Nagender Punna Etsuko Tokunaga Prof. Dr. Norio Shibata Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐Sulfinylimines ChemistryOpen flow chemistry trifluoromethyl fluoroform micro-flow gaseous |
| title | Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐Sulfinylimines |
| title_full | Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐Sulfinylimines |
| title_fullStr | Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐Sulfinylimines |
| title_full_unstemmed | Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐Sulfinylimines |
| title_short | Gas/Liquid‐Phase Micro‐Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N‐Sulfinylimines |
| title_sort | gas liquid phase micro flow trifluoromethylation using fluoroform trifluoromethylation of aldehydes ketones chalcones and n sulfinylimines |
| topic | flow chemistry trifluoromethyl fluoroform micro-flow gaseous |
| url | https://doi.org/10.1002/open.201800286 |
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