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Herein we report the development of a photocatalytic strategy for the divergent preparation of functionalized bicyclo1.1.1pentylamines. This approach exploits, for the first time, the ability of nitrogen-radicals to undergo strain-release reaction with 1.1.1propellane. 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.
Kim et al. (Fri,) studied this question.