Annulative π-Extension (APEX): An Enabling Reaction for Rapid Access to Fused Aromatics, Heteroaromatics, and Nanographenes

Hideto Ito,* Kyohei Ozaki, and Kenichiro Itami*
Angew. Chem. Int. Ed.
 2017, 56, 11144–11164.. DOI: 10.1002/anie.201701058.

[APEX reaction]

The annulative πextension (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.


Comments by Dr. Hideto Ito (First author):
I and Dr. Kyohei Ozaki summarize the definition, scope, aspect and outlook of new reaction concept “APEX” for the rapid and efficient synthesis of π-extended polycyclicl aromatic hydrocarbons, nanographenes and π-extended heteroaromatics and their late-stage functionalizations. While there are a lot of examples of APEX of reactive heteroaromatics, the APEX reaction of benzenes, naphthalenes and PHAs are very rare even if our earyl examples were included.

I was so glad to hear one referee’s tribute comments in the review stage of this manuscript;

I wholeheartedly support publication of this review. Reminiscent of Sharpless’ defining review on the concept of Click Chemistry, Ito, Ozaki and Itami clearly lay out the conceptual basis, background, development and outlook of annulative pi-extension as a distinct class of reactions.

APEX is not one of reaction type but the reaction concept. Indeed, many researchers have achieved various APEX reactions by ulirizing Fridel–Crafts reaction、Diels-Alder reaction、C–H bond activation and so on. While there are not many examples of APEX reaction, recently, I found some researchers start to use a term “APEX” in ther papers. I hope the further development of APEX chemistry in the near future. Of course, we have to keep being “pioneers” in the APEX chemistry.

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