4.8 Review

Annulative π-Extension (APEX): Rapid Access to Fused Arenes, Heteroarenes, and Nanographenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 37, Pages 11144-11164

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701058

Keywords

annulation; arenes; C-H functionalization; condensation; heterocycles

Funding

  1. ERATO program of the JST
  2. JSPS KAKENHI [JP26810057, JP16H00907]
  3. World Premier International Research Center (WPI) Initiative (Japan)
  4. Grants-in-Aid for Scientific Research [16H00907, 17K19155] Funding Source: KAKEN

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The annulative p-extension (APEX) reaction has the potential to have a tremendous impact on the fields of materials science and bioimaging, as well as on the pharmaceutical/agrochemical industries, since it allows access to fused aromatic systems from relatively simple aromatic compounds in a single step. Typically, an APEX reaction facilitates a one-pot p-extension without the need to prefunctionalize the aromatic compounds. This advantageous feature is extremely useful for tuning and modifying molecular properties in the last step of a synthesis. In this Review, the progress and applications of APEX reactions of unfunctionalized arenes and heteroarenes are described.

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