O-, N- and C-bicyclopentylation using thianthrenium reagents

نویسندگان

چکیده

Abstract Rigid 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs) are linear bioisosteres for para -substituted benzene rings in drug development and can lead to an improved pharmacokinetic profile. The construction of BCPs commonly requires the cumbersome use labile [1.1.1]propellane solution, more stable reagents do not show versatile reactivity propellane itself. Here we report thianthrenium-based BCP practical O -, N - C -alkylation reactions that expand scope bicyclopentylation beyond any other reagent, including [1.1.1]propellane. redox stereoelectronic properties thianthrene scaffold relevant both synthesis BCP-thianthrenium via strain release as well their subsequent reactivity. weak exocyclic C–S bond undergo selective mesolytic cleavage upon single-electron reduction produce radicals engage transition metal-mediated C–O, C–N C–C formations, even at a late stage multistep with wide variety functional groups present.

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ژورنال

عنوان ژورنال: Nature Synthesis

سال: 2023

ISSN: ['2731-0582']

DOI: https://doi.org/10.1038/s44160-023-00277-8