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Deconstructive fluorination of cyclic amines by carbon-carbon cleavage.

ABSTRACT: Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp3)-C(sp3) bond cleavage and functionalization have less precedent. Here we report the use of deconstructive fluorination to access mono- and difluorinated amine derivatives by C(sp3)-C(sp3) 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.

SUBMITTER: Roque JB

PROVIDER: S-EPMC6287955 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Deconstructive fluorination of cyclic amines by carbon-carbon cleavage.

Roque Jose B JB Kuroda Yusuke Y Göttemann Lucas T LT Sarpong Richmond R

Science (New York, N.Y.) 20180701 6398

Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp3)-C(sp3) bond cleavage and functionalization have less precedent. Here we report the use of deconstructive fluorination to access mono- and difluorinated amine derivatives by C(sp3)-C(sp3) bond cleavage in saturated nitrogen heterocycles such as piperidines and pyrrolidines. Silver-mediated ring-opening fluorination usin ...[more]

PMID: 30002251

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