Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process

Abstract

A new Cu(II)-catalyzed annulation–cyanotrifluoromethylation of 1,6-enynes with Togni's reagent and trimethylsilyl cyanide (TMSCN) has been established, enabling the direct construction of trifluoromethylated 1-indanones with an all-carbon quaternary center in good yields. This reaction was performed by using low-cost Cu(OTf)2 as the catalyst and Togni's reagent as both the radical initiator and a CF3 source, providing an efficient protocol for building up an 1-indanone framework with wide functional group compatibility. The reaction mechanism was proposed through a radical triggered addition/5-exo-dig cyclization/oxidation/nucleophilic cascade.

Description

© Copyright © 2020 Zhang, Hao, Cai, Li, Tu and Jiang. cc-by

Keywords

1, 1-indanones, 6-enynes, annulation–difunctionalization, Cu(II) catalysis, cyanotrifluoromethylation

Citation

Zhang, T.-S., Hao, W.-J., Cai, P.-J., Li, G., Tu, S.-J., & Jiang, B.. 2020. Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process. Frontiers in Chemistry, 8. https://doi.org/10.3389/fchem.2020.00234

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