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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Published in:Organic letters 2021-02, Vol.23 (3), p.1044-1048
Main Authors: Zhu, Deng, Luo, Hui-Yun, Chen, Zhi-Min
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cited_by cdi_FETCH-LOGICAL-a411t-b98c016bba0e4f83817e336f8160cdfa5712b8e212cd2dbd6b9f3e66270b8d3b3
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creator Zhu, Deng
Luo, Hui-Yun
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description 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.
doi_str_mv 10.1021/acs.orglett.0c04236
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title Selenium-Catalyzed Trifluoromethylsulfinylation/Rearrangement of Allylic and Propargylic Alcohols: Access to Allylic and Allenic Triflones
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