Metal-Free Photoredox Four-Component Strategy to 1,3-Functionalized BCP Derivatives

Trifluoromethyl bicyclo[1.1.1]­pentanes (BCPs) have attracted significant attention from the scientific community and pharmaceutical industries due to their advantageous physicochemical properties as arene bioisosteres. Initial photoredox perfluoroalkylation of [1.1.1]­propellane triggers the tandem...

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Bibliographic Details
Published in:Organic letters 2023-07, Vol.25 (28), p.5308-5313
Main Authors: Srinivasu, Vinjamuri, Das, Debabrata, Chandu, Palasetty, Ghosh, Krishna Gopal, Sureshkumar, Devarajulu
Format: Article
Language:English
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Summary:Trifluoromethyl bicyclo[1.1.1]­pentanes (BCPs) have attracted significant attention from the scientific community and pharmaceutical industries due to their advantageous physicochemical properties as arene bioisosteres. Initial photoredox perfluoroalkylation of [1.1.1]­propellane triggers the tandem reaction to the perfluoroalkyl BCP radical followed by Giese addition to an in situ generated electron-deficient alkene by Knoevenagel condensation in a four-component fashion to form 1,3-functionalized BCPs. This strategy provides easy access to various 1,3-functionalized perfluoroalkyl BCP derivatives with the added advantage of nitrile group as a functional handle to diversified transformations. This methodology offers scalability and late-stage derivatization of drug molecules with high chemoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01877