CuSO4-Catalyzed dual annulation to synthesize O, S or N-containing tetracyclic heteroacenes

In this work, CuSO4 is utilized as a practical redox catalyst for tandem dual annulation in the synthesis of indole-fused tetracyclic heteroacenes, which are important skeletons in both medicinal chemistry and materials chemistry. The preparation of such skeletons in a convenient and efficient manne...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-04, Vol.56 (29), p.4063-4066
Main Authors: Xiang-Huan Shan, Yang, Bo, Qu, Jian-Ping, Yan-Biao Kang
Format: Article
Language:English
Subjects:
Biological properties
Chemical reactions
Chemical synthesis
Copper sulfate
Crystallography
Halides
Optoelectronics
Organic chemistry
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Summary:In this work, CuSO4 is utilized as a practical redox catalyst for tandem dual annulation in the synthesis of indole-fused tetracyclic heteroacenes, which are important skeletons in both medicinal chemistry and materials chemistry. The preparation of such skeletons in a convenient and efficient manner is in high demand. This method realizes the modular synthesis of benzofuro-, benzothieno-, and indoloindoles from abundant feedstocks such as 2-halobenzyl halides and nitrile derivatives in up to 99% yields, providing a rapid access to diverse indole-fused heteroacenes with biological or optoelectronic properties.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc01172j