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Helicene Chemistry pp 71–86Cite as

Diels–Alder and Friedel–Crafts-Type Reactions

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Abstract

In this chapter, the synthesis of helicenes via Diels–Alder reactions and Friedel–Crafts-type reactions is described. In the first section, the Diels–Alder reactions are discussed, which not only are practical methods for the preparation of symmetric helicenes, but also can be utilized for the large-scale synthesis of helicene derivatives, especially helicene quinones. The major limitation of the methodology is the limited types of dienes and dienophiles. In the second section, Friedel–Crafts-type reaction is introduced, which is one of the first reported and also a useful strategy for the synthesis of helicenes. The synthesis usually needs less than five steps with moderate-to-good yields. Similarly, heterohelicenes including azahelicenes and phosphahelicene can be synthesized by double Friedel–Crafts acylation or phospha-Friedel–Crafts reaction. Two points should be taken into account in Friedel–Crafts-type reaction: (1) polar unsaturated bonds should be well designed and incorporated into the substrates; (2) it is better to introduce the directing or blocking groups to promote the regioselectivity.

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Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China

    Chuan-Feng Chen & Yun Shen

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  1. Chuan-Feng Chen
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  2. Yun Shen
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Correspondence to Chuan-Feng Chen .

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Chen, CF., Shen, Y. (2017). Diels–Alder and Friedel–Crafts-Type Reactions. In: Helicene Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-53168-6_4

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