Deconstructive fluorination of cyclic amines by carbon-carbon cleavage

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

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2018-07, Vol.361 (6398), p.171-174
Main Authors: Roque, Jose B, Kuroda, Yusuke, Göttemann, Lucas T, Sarpong, Richmond
Format: Article
Language:English
Subjects:
Amines
Bonding strength
Carbon
Carbon cycle
Cleavage
Fluorination
Fluorine
Nitrogen
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Summary:Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp )-C(sp ) 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 )-C(sp ) 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.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.aat6365