Silver-Mediated Oxidative Aliphatic CH Trifluoromethylthiolation
The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver‐based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional‐group compa...
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| Published in | Angewandte Chemie International Edition Vol. 54; no. 13; pp. 4065 - 4069 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
23.03.2015
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 1521-3773 |
| DOI | 10.1002/anie.201411807 |
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| Abstract | The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver‐based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional‐group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural‐product derivatives.
The silver‐mediated trifluoromethylthiolation of unactivated aliphatic CH bonds is reported. The reaction is operationally simple, amenable to gram‐scale synthesis, and can be employed for the late‐stage trifluoromethylthiolation of complex small molecules. |
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| AbstractList | The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives.The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives. The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver‐based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional‐group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural‐product derivatives. The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic C--H bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives. The silver-mediated trifluoromethylthiolation of unactivated aliphatic C--H bonds is reported. The reaction is operationally simple, amenable to gram-scale synthesis, and can be employed for the late-stage trifluoromethylthiolation of complex small molecules. The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic C-H bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives. The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver‐based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional‐group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural‐product derivatives. The silver‐mediated trifluoromethylthiolation of unactivated aliphatic CH bonds is reported. The reaction is operationally simple, amenable to gram‐scale synthesis, and can be employed for the late‐stage trifluoromethylthiolation of complex small molecules. |
| Author | Tang, Pingping Zhang, Xiaofei Guo, Shuo |
| Author_xml | – sequence: 1 givenname: Shuo surname: Guo fullname: Guo, Shuo organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071 (China) – sequence: 2 givenname: Xiaofei surname: Zhang fullname: Zhang, Xiaofei organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071 (China) – sequence: 3 givenname: Pingping surname: Tang fullname: Tang, Pingping email: ptang@nankai.edu.cn organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071 (China) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25714354$$D View this record in MEDLINE/PubMed |
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| Keywords | radicals trifluoromethylthiolation UNACTIVATED ALKENES AQUEOUS-SOLUTION ELEMENTAL SULFUR C-H activation ARYL BORONIC ACIDS HYPERVALENT IODINE REAGENT ALPHA-FLUORINATED ETHERS COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION ELECTROPHILIC TRIFLUOROMETHANESULFANYLATION SELECTIVE TRIFLUOROMETHYLTHIOLATION synthetic methods fluorine CARBOXYLIC-ACIDS CH activation |
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| Notes | ArticleID:ANIE201411807 NSFC - No. 21402098; No. 21421062 We gratefully acknowledge the State Key Laboratory of Elemento-Organic Chemistry for generous start-up financial support. This work was supported by the "1000 Youth Talents Plan", the NSFC (21402098, 21421062), and the Natural Science Foundation of Tianjin (13JCYBJC36500). Prof. Jennifer M. Murphy is greatly acknowledged for helpful comments. State Key Laboratory of Elemento-Organic Chemistry Natural Science Foundation of Tianjin - No. 13JCYBJC36500 1000 Youth Talents Plan ark:/67375/WNG-SX8LV6F4-W istex:C395ABFEE3D2F9507A473C9D70EB09B73512E27C We gratefully acknowledge the State Key Laboratory of Elemento‐Organic Chemistry for generous start‐up financial support. This work was supported by the “1000 Youth Talents Plan”, the NSFC (21402098, 21421062), and the Natural Science Foundation of Tianjin (13JCYBJC36500). Prof. Jennifer M. Murphy is greatly acknowledged for helpful comments. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag Wiley |
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| SSID | ssj0028806 |
| Score | 2.531706 |
| Snippet | The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver‐based reagent. The reaction... The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic C-H bonds employs a silver-based reagent. The reaction... The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver-based reagent. The reaction... The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic C--H bonds employs a silver-based reagent. The reaction... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref wiley istex |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 4065 |
| SubjectTerms | Aliphatic compounds Amino Acids - chemistry Biological Products - chemistry Chemistry Chemistry, Multidisciplinary Compatibility CH activation Derivatives fluorine Hydrocarbons, Fluorinated - chemical synthesis Indicators and Reagents Models, Molecular Molecular Conformation Natural products Oxidation-Reduction Physical Sciences radicals Science & Technology Silver Compounds - chemistry Sulfates - chemistry Sulfhydryl Compounds - chemical synthesis Synthesis synthetic methods trifluoromethylthiolation |
| Title | Silver-Mediated Oxidative Aliphatic CH Trifluoromethylthiolation |
| URI | https://api.istex.fr/ark:/67375/WNG-SX8LV6F4-W/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201411807 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000351204600040 https://www.ncbi.nlm.nih.gov/pubmed/25714354 https://www.proquest.com/docview/1664441603 https://www.proquest.com/docview/1701046122 |
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