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Creators/Authors contains: "Phillips, Eric M"

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  1. ; ; ; ; ; ; ; ; ; ; et al (, Journal of the American Chemical Society)
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  2. ; ; ; ; ; ; ; ; ; (, Journal of the American Chemical Society)
    Lloyd-Jones, Guy (Ed.)
    Methods to synthesize diverse collections of sub- stituted piperidines are valuable due to the prevalence of this heterocycle in pharmaceutical compounds. Here, we present a general strategy to access N-(hetero)arylpiperidines using a pyridine ring-opening and ring-closing approach via Zincke imine inter- mediates. This process generates pyridinium salts from a wide variety of substituted pyridines and (heteroaryl)anilines; hydro- genation reactions and nucleophilic additions then access the N- (hetero)arylpiperidine derivatives. We successfully applied high- throughput experimentation (HTE) using pharmaceutically relevant pyridines and (heteroaryl)anilines as inputs and developed a one-pot process using anilines as nucleophiles in the pyridinium salt-forming processes. This strategy is viable for generating piperidine libraries and applications such as the convergent coupling of complex fragments. 
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