4.8 Article

Insertion of Arynes into Thioureas: A New Amidine Synthesis

Journal

ORGANIC LETTERS
Volume 13, Issue 18, Pages 4946-4949

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202049v

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Funding

  1. EPSRC
  2. EPSRC [EP/G007519/1] Funding Source: UKRI
  3. Engineering and Physical Sciences Research Council [EP/G007519/1] Funding Source: researchfish

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Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal pi-insertion into the C=S bond. The reaction contrasts with that of ureas, which proceeds via benzyne sigma-insertion into the C-N bond, and represents a new, operationally simple route to functionalized amidines.

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