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Published on: January 30, 2015
Deconstructive fluorination of cyclic amines by carbon-carbon cleavage
Jose B Roque1, Yusuke Kuroda1, Lucas T Göttemann1
1Department of Chemistry, University of California, Berkeley, CA 94720, USA.
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.
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