Copper-Catalyzed Preparation of Benzo[3,4]indolo[1,2‑b]isoquinoline-8-ones and Photoluminescence Exploration

A facile synthesis of benzo­[3,4]­indolo­[1,2-b]­isoquinolin-8-ones is described. Under copper catalysis, the reaction proceeds with a high efficiency and a broad reaction scope. A deuteration experiment shows that the KIE value is 2.85. From the results on mechanism studies, copper-catalyzed C–H ac...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-08, Vol.85 (15), p.9614-9621
Main Authors: Hua, Yiwen, Chen, Zi-Yan, Diao, Hanying, Zhang, Lianpeng, Qiu, Guanyinsheng, Gao, Xiaoxing, Zhou, Hongwei
Format: Article
Language:English
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Summary:A facile synthesis of benzo­[3,4]­indolo­[1,2-b]­isoquinolin-8-ones is described. Under copper catalysis, the reaction proceeds with a high efficiency and a broad reaction scope. A deuteration experiment shows that the KIE value is 2.85. From the results on mechanism studies, copper-catalyzed C–H activation, intramolecular cis-addition of alkynes, and reductive elimination are involved. Moreover, this skeleton is indeed a new fluorophore, and its photophysical properties are also investigated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00936