4.8 Article

Aryl(TMP)iodonium Tosylate Reagents as a Strategic Entry Point to Diverse Aryl Intermediates: Selective Access to Arynes

Journal

ORGANIC LETTERS
Volume 23, Issue 12, Pages 4813-4817

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01534

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Funding

  1. Portland State University (Faculty Enhancement Award)
  2. National Science Foundation [CHE 1856705, MRI 1828573]

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Controlling reaction pathways selectively leads to a broad scope of arenes and arynophiles, offering efficient access to diverse arene chemical space and biologically active compounds with high yields.
Arenes are broadly found motifs in societally important molecules. Access to diverse arene chemical space is critically important, and the ability to do so from common reagents is highly desirable. Aryl(TMP)iodonium tosylates provide one such access point to arene chemical space via diverse aryl intermediates. Here we demonstrate that controlling reaction pathways selectively leads to arynes with a broad scope of arenes and arynophiles (24 examples, 70% average yield) and efficient access to biologically active compounds.

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