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Synthesis
DOI: 10.1055/s-0040-1720139
DOI: 10.1055/s-0040-1720139
feature
Visible-Light-Induced Photoredox Construction of Trifluoromethylated Quaternary All-Carbon Centers and Tertiary Alcohols via C(sp3)–Si Bond Cleavage
This work is supported by the National Natural Science Foundation of China (NSFC) (22471063), the Natural Science Foundation of Henan Province (242300421351, 222102310562) and the Henan Postdoctoral Science Foundation (202103087). We also acknowledge financial support from the Henan Key Laboratory of Organic Functional Molecules and Drug Innovation.
Abstract
The construction of trifluoromethylated quaternary carbon centers and tertiary alcohols is realized by organo-photoredox catalysis. The process proceeds via visible-light-induced C(sp3)–Si bond cleavage for the generation of α-trifluoromethylated benzyl radicals, which are readily trapped by electron-deficient alkenes with excellent regioselectivity for the construction of trifluoromethylated quaternary all-carbon centers. The α-difluoromethyl counterparts are also suitable for this radical conjugate addition. Furthermore, the in situ oxidation of these α-trifluoromethylated radicals with O2 from air affords tertiary alcohols in high yields, which extends the Fleming–Tamao reaction to tertiary carbon systems.
Key words
visible-light-induced - trifluoromethylated quaternary carbon centers - tertiary alcohols - C(sp3)–Si bond cleavage - transition-metal-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720139.
- Supporting Information
- CIF File
Publication History
Received: 26 July 2024
Accepted after revision: 13 September 2024
Article published online:
10 October 2024
© 2024. Thieme. All rights reserved
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