AI Article Synopsis
- Developed a new photocatalytic method for creating functionalized bicyclo[1.1.1]pentylamines using nitrogen-radicals and [1.1.1]propellane, which had not been previously explored.
- This method takes advantage of the unique properties of nitrogen-radicals and the effects of strong polar interactions during the reaction process.
- The approach can integrate with other components and create new amino-functionalized structures that could be useful in drug development, particularly as analogs to p-substituted anilines.
Article 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.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7318212 | PMC |
| http://dx.doi.org/10.1002/anie.202000140 | DOI Listing |
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