Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 21, Pages 8225-8231Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202000140
Keywords
amino-functionalization; bioisosteres; nitrogen radicals; strain-release
Categories
Funding
- EPSRC [EP/P004997/1]
- European Research Council [758427]
- Marie Curie Actions for a Fellowship [842422]
- Deanship of Scientific Research at King Faisal University [186266]
- EPSRC [EP/P004997/1] Funding Source: UKRI
- Marie Curie Actions (MSCA) [842422] Funding Source: Marie Curie Actions (MSCA)
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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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