4.8 Article

Selective and Multiple Functionalization of Pyridines and Alkaloids via Mg- and Zn-Organometallic Intermediates

Journal

ORGANIC LETTERS
Volume 13, Issue 9, Pages 2306-2309

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol200563j

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Funding

  1. European Research Council under the European Community [FP7/2007-2013]
  2. ERC [227763]
  3. Deutsche Forschungsgemeinschaft (DFG)
  4. European Research Council (ERC) [227763] Funding Source: European Research Council (ERC)

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Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF3 center dot OEt2. A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of IMP bases in the presence or absence of BF3 center dot OEt2.

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