Journal
SCIENCE
Volume 361, Issue 6398, Pages 171-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aat6365
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Funding
- National Institutes of Health [NIGMS RO1 086374]
- NIH [NIGMS RO1 086374]
- Japan Society for the Promotion of Science (JSPS)
- LMU PROSA
- DAAD
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM086374] Funding Source: NIH RePORTER
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Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp(3))-C(sp(3)) bond cleavage and functionalization have less precedent. Here we report the use of deconstructive fluorination to access mono-and difluorinated amine derivatives by C(sp(3))-C(sp(3)) bond cleavage in saturated nitrogen heterocycles such as piperidines and pyrrolidines. Silver-mediated ring-opening fluorination using Selectfluor highlights a strategy for cyclic amine functionalization and late-stage skeletal diversification, establishing cyclic amines as synthons for amino alkyl radicals and providing synthetic routes to valuable building blocks.
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