Divergent Strain‐Release Amino‐Functionalization of (1.1.1) Propellane with Electrophilic Nitrogen‐Radicals

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Abstract: Herein we report the development of a photocatalytic strategy for the divergent preparation of functionalized bicyclo[1.1.1]pentylamines. This approach exploits, for the first time, the ability of nitrogen‐radicals to undergo strain‐release reaction with [1.1.1]propellane. This reactivity is facilitated by the electrophilic nature of these open‐shell intermediates and the presence of strong polar effects in the transition‐state for C−N bond formation/ring‐opening. With the aid of a simple reductive quenching photoredox cycle, we have successfully harnessed this novel radical strain‐release amination as part of a multicomponent cascade compatible with several external trapping agents. Overall, this radical strategy enables the rapid construction of novel amino‐functionalized building blocks with potential application in medicinal chemistry programs as p‐substituted aniline bioisosteres.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Divergent Strain‐Release Amino‐Functionalization of (1.1.1) Propellane with Electrophilic Nitrogen‐Radicals ; volume:132 ; number:21 ; year:2020 ; pages:8302-8308 ; extent:7
Angewandte Chemie ; 132, Heft 21 (2020), 8302-8308 (gesamt 7)

Creator: Kim, Ji Hye
Ruffoni, Alessandro
Al‐Faiyz, Yasair S. S.
Sheikh, Nadeem S.
Leonori, Daniele

DOI: 10.1002/ange.202000140

URN: urn:nbn:de:101:1-2022052812290978073573

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:33 AM CEST

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Kim, Ji Hye
Ruffoni, Alessandro
Al‐Faiyz, Yasair S. S.
Sheikh, Nadeem S.
Leonori, Daniele

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