Access to Trifluoromethylketones from Alkyl Bromides and Trifluoroacetic Anhydride by Photocatalysis
Aliphatic trifluoromethyl ketones are a type of unique fluorine‐containing subunit which play a significant role in altering the physical and biological properties of molecules. Catalytic methods to provide direct access to aliphatic trifluoromethyl ketones are highly desirable yet remain underdevel...
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| Vydané v: | Angewandte Chemie International Edition Ročník 62; číslo 38; s. e202308732 |
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| Hlavní autori: | , , , |
| Médium: | Journal Article |
| Jazyk: | English |
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WEINHEIM
Wiley
18.09.2023
Wiley Subscription Services, Inc |
| Vydanie: | International ed. in English |
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| ISSN: | 1433-7851, 1521-3773, 1521-3773 |
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| Abstract | Aliphatic trifluoromethyl ketones are a type of unique fluorine‐containing subunit which play a significant role in altering the physical and biological properties of molecules. Catalytic methods to provide direct access to aliphatic trifluoromethyl ketones are highly desirable yet remain underdeveloped, partially owing to the high reactivity and instability of trifluoroacetyl radical. Herein, we report a photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible‐light and halogen‐atom‐transfer catalysis, followed by an enabling radical‐radical cross‐coupling of an alkyl radical with a stabilized trifluoromethyl radical. The reaction provides straightforward access to aliphatic trifluoromethyl ketones from readily available and cost‐effective alkyl halides and trifluoroacetic anhydride (TFAA). |
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| AbstractList | Aliphatic trifluoromethyl ketones are a type of unique fluorine‐containing subunit which play a significant role in altering the physical and biological properties of molecules. Catalytic methods to provide direct access to aliphatic trifluoromethyl ketones are highly desirable yet remain underdeveloped, partially owing to the high reactivity and instability of trifluoroacetyl radical. Herein, we report a photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible‐light and halogen‐atom‐transfer catalysis, followed by an enabling radical‐radical cross‐coupling of an alkyl radical with a stabilized trifluoromethyl radical. The reaction provides straightforward access to aliphatic trifluoromethyl ketones from readily available and cost‐effective alkyl halides and trifluoroacetic anhydride (TFAA). Aliphatic trifluoromethyl ketones are a type of unique fluorine-containing subunit which play a significant role in altering the physical and biological properties of molecules. Catalytic methods to provide direct access to aliphatic trifluoromethyl ketones are highly desirable yet remain underdeveloped, partially owing to the high reactivity and instability of trifluoroacetyl radical. Herein, we report a photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible-light and halogen-atom-transfer catalysis, followed by an enabling radical-radical cross-coupling of an alkyl radical with a stabilized trifluoromethyl radical. The reaction provides straightforward access to aliphatic trifluoromethyl ketones from readily available and cost-effective alkyl halides and trifluoroacetic anhydride (TFAA).Aliphatic trifluoromethyl ketones are a type of unique fluorine-containing subunit which play a significant role in altering the physical and biological properties of molecules. Catalytic methods to provide direct access to aliphatic trifluoromethyl ketones are highly desirable yet remain underdeveloped, partially owing to the high reactivity and instability of trifluoroacetyl radical. Herein, we report a photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible-light and halogen-atom-transfer catalysis, followed by an enabling radical-radical cross-coupling of an alkyl radical with a stabilized trifluoromethyl radical. The reaction provides straightforward access to aliphatic trifluoromethyl ketones from readily available and cost-effective alkyl halides and trifluoroacetic anhydride (TFAA). Aliphatic trifluoromethyl ketones are a type of unique fluorine‐containing subunit which play a significant role in altering the physical and biological properties of molecules. Catalytic methods to provide direct access to aliphatic trifluoromethyl ketones are highly desirable yet remain underdeveloped, partially owing to the high reactivity and instability of trifluoroacetyl radical. Herein, we report a photocatalytic synthesis of trifluoromethyl ketones from alkyl bromides with trifluoroacetic anhydride. The reaction features dual visible‐light and halogen‐atom‐transfer catalysis, followed by an enabling radical‐radical cross‐coupling of an alkyl radical with a stabilized trifluoromethyl radical. The reaction provides straightforward access to aliphatic trifluoromethyl ketones from readily available and cost‐effective alkyl halides and trifluoroacetic anhydride (TFAA).In memory of Professor Xiyan Lu. |
| ArticleNumber | 202308732 |
| Author | Du, Yi‐Dan Zeng, Xian‐Wang Shu, Wei Du, Hai‐Wu |
| Author_xml | – sequence: 1 givenname: Hai‐Wu surname: Du fullname: Du, Hai‐Wu organization: Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and Technology Shenzhen 518055 Guangdong P. R. China – sequence: 2 givenname: Yi‐Dan surname: Du fullname: Du, Yi‐Dan organization: Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and Technology Shenzhen 518055 Guangdong P. R. China – sequence: 3 givenname: Xian‐Wang surname: Zeng fullname: Zeng, Xian‐Wang organization: Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and Technology Shenzhen 518055 Guangdong P. R. China – sequence: 4 givenname: Wei orcidid: 0000-0003-0890-2634 surname: Shu fullname: Shu, Wei organization: Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and Technology Shenzhen 518055 Guangdong P. R. China, State Key Laboratory of Elemento-Organic Chemistry Nankai University 300071 Tianjin P. R. China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37534823$$D View this record in MEDLINE/PubMed |
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| Keywords | Anhydrides CATALYSIS Photocatalysis STRATEGY Radical-Radical Coupling ALCOHOLS KETONES ALKENES Trifluoroacetylation FLUORINE GENERATION RADICALS INHIBITORS Halogen Atom Transfer DERIVATIVES |
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| Snippet | Aliphatic trifluoromethyl ketones are a type of unique fluorine‐containing subunit which play a significant role in altering the physical and biological... Aliphatic trifluoromethyl ketones are a type of unique fluorine-containing subunit which play a significant role in altering the physical and biological... |
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| SubjectTerms | Aliphatic compounds Anhydrides Biological properties Bromides Catalysis Chemistry Chemistry, Multidisciplinary Coupling (molecular) Cross coupling Fluorine Halides Ketones Photocatalysis Physical Sciences Science & Technology Trifluoroacetic anhydride Trifluoroacetyl |
| Title | Access to Trifluoromethylketones from Alkyl Bromides and Trifluoroacetic Anhydride by Photocatalysis |
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