Deconstructive fluorination of cyclic amines by carbon-carbon cleavage.
basic_science · Level V
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- Record sourced from PubMed, PMID 30002251.
- Also identified by DOI 10.1126/science.aat6365 and PMC identifier 6287955.
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Abstract
Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp<sup>3</sup>)-C(sp<sup>3</sup>) 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<sup>3</sup>)-C(sp<sup>3</sup>) 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.