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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.

SUBMITTER: Zhang TS

PROVIDER: S-EPMC7180230 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Zhang Tian-Shu TS Hao Wen-Juan WJ Cai Pei-Jun PJ Li Guigen G Tu Shu-Jiang SJ Jiang Bo B

Frontiers in chemistry 20200417

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 fram ...[more]

PMID: 32363174

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