Synthesis of\nAlkyl Bis(trifluoromethyl)carbinols via\nFe-LMCT-Enabled Hydrobis(trifluoromethyl)carbinolation of Alkenes

Bis(trifluoromethyl)carbinols are valuable pharmacophores,\nyet\ntheir synthesis is challenging, largely due to a scarcity of safe\nand effective bis(trifluoromethyl)carbinolation reagents. Here, we\nrealized the hydrobis(trifluoromethyl)carbinolation of alkenes, utilizing\nstable and readily accessible 2,2-bis(trifluoromethyl)glycolic acid\nas a source of both the bis(trifluoromethyl)carbinol unit and a hydrogen\natom. This process leverages a photoinduced Fe-LMCT-enabled radical\ndecarboxylation process that generates a key bis(trifluoromethyl)carbinol\nradical intermediate. Our mild protocol facilitates the synthesis\nof a diverse range of alkyl bis(trifluoromethyl)carbinols, including\nstructurally complex molecules with pharmaceutical relevance.

Publication Details

Journal
Figshare
Published
2024-10-30
DOI
https://doi.org/10.1021/acs.orglett.4c03609.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
Field-Weighted Citation Impact
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article

Synthesis of\nAlkyl Bis(trifluoromethyl)carbinols via\nFe-LMCT-Enabled Hydrobis(trifluoromethyl)carbinolation of Alkenes

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Synthesis of\nAlkyl Bis(trifluoromethyl)carbinols via\nFe-LMCT-Enabled Hydrobis(trifluoromethyl)carbinolation of Alkenes

article en

Abstract

Bis(trifluoromethyl)carbinols are valuable pharmacophores,\nyet\ntheir synthesis is challenging, largely due to a scarcity of safe\nand effective bis(trifluoromethyl)carbinolation reagents. Here, we\nrealized the hydrobis(trifluoromethyl)carbinolation of alkenes, utilizing\nstable and readily accessible 2,2-bis(trifluoromethyl)glycolic acid\nas a source of both the bis(trifluoromethyl)carbinol unit and a hydrogen\natom. This process leverages a photoinduced Fe-LMCT-enabled radical\ndecarboxylation process that generates a key bis(trifluoromethyl)carbinol\nradical intermediate. Our mild protocol facilitates the synthesis\nof a diverse range of alkyl bis(trifluoromethyl)carbinols, including\nstructurally complex molecules with pharmaceutical relevance.

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Mycorrhizal Fungi and Plant Interactions
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