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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Frontiers Media S.A.
2020-04-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00234/full |
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doaj-c94e966ff48748c092016e46a0ff76472020-11-25T02:55:57ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-04-01810.3389/fchem.2020.00234526436Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical ProcessTian-Shu Zhang0Wen-Juan Hao1Pei-Jun Cai2Guigen Li3Guigen Li4Shu-Jiang Tu5Bo Jiang6School of Chemical Engineering & Technology, China University of Mining and Technology, Xuzhou, ChinaJiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, ChinaSchool of Chemical Engineering & Technology, China University of Mining and Technology, Xuzhou, ChinaCollaborative Innovation Center of Chemistry for Life Sciences, Institute of Chemistry and BioMedical Sciences, Nanjing University, Nanjing, ChinaDepartment of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, United StatesJiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, ChinaJiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, ChinaA 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.https://www.frontiersin.org/article/10.3389/fchem.2020.00234/fullCu(II) catalysisannulation–difunctionalizationcyanotrifluoromethylation16-enynes1-indanones |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Tian-Shu Zhang Wen-Juan Hao Pei-Jun Cai Guigen Li Guigen Li Shu-Jiang Tu Bo Jiang |
| spellingShingle |
Tian-Shu Zhang Wen-Juan Hao Pei-Jun Cai Guigen Li Guigen Li Shu-Jiang Tu Bo Jiang Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process Frontiers in Chemistry Cu(II) catalysis annulation–difunctionalization cyanotrifluoromethylation 1 6-enynes 1-indanones |
| author_facet |
Tian-Shu Zhang Wen-Juan Hao Pei-Jun Cai Guigen Li Guigen Li Shu-Jiang Tu Bo Jiang |
| author_sort |
Tian-Shu Zhang |
| title |
Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process |
| title_short |
Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process |
| title_full |
Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process |
| title_fullStr |
Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process |
| title_full_unstemmed |
Copper-Catalyzed Annulation–Cyanotrifluoromethylation of 1,6-Enynes Toward 1-Indanones via a Radical Process |
| title_sort |
copper-catalyzed annulation–cyanotrifluoromethylation of 1,6-enynes toward 1-indanones via a radical process |
| publisher |
Frontiers Media S.A. |
| series |
Frontiers in Chemistry |
| issn |
2296-2646 |
| publishDate |
2020-04-01 |
| description |
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. |
| topic |
Cu(II) catalysis annulation–difunctionalization cyanotrifluoromethylation 1 6-enynes 1-indanones |
| url |
https://www.frontiersin.org/article/10.3389/fchem.2020.00234/full |
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