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

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

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 perf...

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Bibliographic Details
Main Authors: Tian-Shu Zhang, Wen-Juan Hao, Pei-Jun Cai, Guigen Li, Shu-Jiang Tu, Bo Jiang
Format: Article
Language:English
Published: Frontiers Media S.A. 2020-04-01
Series:Frontiers in Chemistry
Subjects:
Cu(II) catalysis
annulation–difunctionalization
cyanotrifluoromethylation
1
6-enynes
1-indanones
Online Access:https://www.frontiersin.org/article/10.3389/fchem.2020.00234/full
Description
Summary: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.
ISSN:2296-2646

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