Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Copper-Catalyzed Trifluoromethylthiolation of Enamines, Indoles, and β‑Keto Esters
A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluorom...
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| Published in | Journal of the American Chemical Society Vol. 135; no. 24; pp. 8782 - 8785 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
19.06.2013
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0002-7863 1520-5126 1520-5126 |
| DOI | 10.1021/ja402455f |
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| Abstract | A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride. |
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| AbstractList | A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF₃S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride. A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride. A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride.A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride. |
| Author | Shibata, Norio Yang, Yu-Dong Azuma, Ayaka Tokunaga, Etsuko Yamasaki, Mikio Shiro, Motoo |
| AuthorAffiliation | Nagoya Institute of Technology Rigaku Corporation |
| AuthorAffiliation_xml | – name: Nagoya Institute of Technology – name: Rigaku Corporation |
| Author_xml | – sequence: 1 givenname: Yu-Dong surname: Yang fullname: Yang, Yu-Dong – sequence: 2 givenname: Ayaka surname: Azuma fullname: Azuma, Ayaka – sequence: 3 givenname: Etsuko surname: Tokunaga fullname: Tokunaga, Etsuko – sequence: 4 givenname: Mikio surname: Yamasaki fullname: Yamasaki, Mikio – sequence: 5 givenname: Motoo surname: Shiro fullname: Shiro, Motoo – sequence: 6 givenname: Norio surname: Shibata fullname: Shibata, Norio email: nozshiba@nitech.ac.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23738814$$D View this record in MEDLINE/PubMed |
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| Snippet | A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various... |
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| SubjectTerms | Amines - chemistry Catalysis Chemistry Chemistry, Multidisciplinary chlorides copper Copper - chemistry esters Esters - chemistry Hydrocarbons, Fluorinated - chemistry indoles Indoles - chemistry Ketones - chemistry Onium Compounds - chemistry Oxidation-Reduction Physical Sciences Science & Technology Sulfhydryl Compounds - chemistry |
| Title | Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Copper-Catalyzed Trifluoromethylthiolation of Enamines, Indoles, and β‑Keto Esters |
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