Synthesis of 1‑Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2‑(2-Alkynylphenyl)acetonitriles and Alkynones

Effective transition-metal-free formal [4+2] benzannulation for the preparation of 1-cyano-3-acylnaphthalenes from 2-(2-alkynylphenyl)­acetonitriles and alkynones through sequential C–C bond coupling has been developed. This protocol is characterized by mild conditions, excellent functional group to...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-06, Vol.84 (12), p.8090-8099
Main Authors: Chen, Lu-Lu, Zhang, Jing-Wen, Yang, Wan-Wan, Fu, Ji-Ya, Zhu, Jun-Yan, Wang, Yan-Bo
Format: Article
Language:English
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Summary:Effective transition-metal-free formal [4+2] benzannulation for the preparation of 1-cyano-3-acylnaphthalenes from 2-(2-alkynylphenyl)­acetonitriles and alkynones through sequential C–C bond coupling has been developed. This protocol is characterized by mild conditions, excellent functional group tolerance, complete regioselectivity, and atom economy. The plausible mechanism, gram-scale synthesis, and further transformations of the product were studied.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00948