Selenium-Catalyzed Trifluoromethylsulfinylation/Rearrangement of Allylic and Propargylic Alcohols: Access to Allylic and Allenic Triflones
A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it...
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| Vydáno v: | Organic letters Ročník 23; číslo 3; s. 1044 - 1048 |
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Amer Chemical Soc
05.02.2021
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| ISSN: | 1523-7060, 1523-7052, 1523-7052 |
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| Abstract | A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [+SCF3] group disproportionation process that forms [+SOCF3] that is in-situ-catalyzed by selenium, and H2O was used as an oxygen source. This reaction features mild reaction conditions and good compatibility of substrates, and it is transition-metal-free. |
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| AbstractList | A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [
SCF
] group disproportionation process that forms [
SOCF
] that is in-situ-catalyzed by selenium, and H
O was used as an oxygen source. This reaction features mild reaction conditions and good compatibility of substrates, and it is transition-metal-free. A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [+SCF3] group disproportionation process that forms [+SOCF3] that is in-situ-catalyzed by selenium, and H2O was used as an oxygen source. This reaction features mild reaction conditions and good compatibility of substrates, and it is transition-metal-free.A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [+SCF3] group disproportionation process that forms [+SOCF3] that is in-situ-catalyzed by selenium, and H2O was used as an oxygen source. This reaction features mild reaction conditions and good compatibility of substrates, and it is transition-metal-free. A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [+SCF3] group disproportionation process that forms [+SOCF3] that is in-situ-catalyzed by selenium, and H2O was used as an oxygen source. This reaction features mild reaction conditions and good compatibility of substrates, and it is transition-metal-free. |
| Author | Chen, Zhi-Min Zhu, Deng Luo, Hui-Yun |
| Author_xml | – sequence: 1 givenname: Deng surname: Zhu fullname: Zhu, Deng organization: Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China – sequence: 2 givenname: Hui-Yun surname: Luo fullname: Luo, Hui-Yun organization: Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China – sequence: 3 givenname: Zhi-Min orcidid: 0000-0002-6988-8955 surname: Chen fullname: Chen, Zhi-Min email: chenzhimin221@sjtu.edu.cn organization: Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33443438$$D View this record in MEDLINE/PubMed |
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| Snippet | A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Selenium-Catalyzed Trifluoromethylsulfinylation/Rearrangement of Allylic and Propargylic Alcohols: Access to Allylic and Allenic Triflones |
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