4.8 Article

TMPZnCl•LiCl: A New Active Selective Base for the Directed Zincation of Sensitive Aromatics and Heteroaromatics

Journal

ORGANIC LETTERS
Volume 11, Issue 8, Pages 1837-1840

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900342a

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Funding

  1. Fonds der Chemischen Industrie
  2. Deutsche Forschungsgerneinschaft (DFG)
  3. European Research Council (ERC)

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A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF via direct zincation using TMPZnCl center dot LiCl, a new exceptionally mild and efficient base. Activated arenes and heteroarenes are metalated at room temperature. Remarkably, sensitive functions such as an aldehyde as well as a nitro group are tolerated, expanding significantly the scope of directed metalations.

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