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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Bibliographic Details
Published in:Organic letters Vol. 23; no. 3; pp. 1044 - 1048
Main Authors: Zhu, Deng, Luo, Hui-Yun, Chen, Zhi-Min
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 05.02.2021
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ISSN:1523-7060, 1523-7052, 1523-7052
Online Access:Get more information
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Summary: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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c04236