Deconstructive fluorination of cyclic amines by carbon-carbon cleavage

Jose B. Roque, Yusuke Kuroda, Lucas T. Göttemann, Richmond Sarpong

Research output: Contribution to journalArticlepeer-review

149 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)171-174
Number of pages4
JournalScience
Volume361
Issue number6398
DOIs
StatePublished - Jul 13 2018
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General

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