4.8 Article

Aryne Relay Chemistry en Route to Aminoarenes: Synthesis of 3-Aminoaryne Precursors via Regioselective Silylamination of 3-(Triflyloxy)arynes

Journal

ORGANIC LETTERS
Volume 18, Issue 23, Pages 6212-6215

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03304

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Funding

  1. JSPS KAKENHI Grant [15H03118, 16H01133, 26350971]
  2. Suntory Foundation for Life Sciences
  3. Platform for Drug Discovery, Informatics, and Structural Life Science of MEXT, Japan
  4. Platform for Drug Discovery, Informatics, and Structural Life Science of AMED, Japan
  5. Grants-in-Aid for Scientific Research [26350971, 16H01133, 15H03118] Funding Source: KAKEN

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A facile synthetic method for preparing 3-amino-2-silylaryl triflates via regioselective silylamination of 3(triflyloxy)arynes with N-silylamines is described. Fluoride mediated generation of 3-aminobenzyne from 3-amino-2-silylphenyl triflate, easily prepared by this method, in the presence of various arynophiles efficiently afforded diverse aniline derivatives, including a 5-aminocoumarin derivative, demonstrating the utility of aryne relay approach.

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