Copper-catalyzed radical trifluoromethylalkynylation of unactivated alkenes with terminal alkynes
•Terminal alkynes are used in trifluoromethylalkynylation of unactivated alkenes.•The design of copper/N,N,N-ligand catalyst ensures its success.•Mild conditions make it operationally simple. A copper-catalyzed three-component radical trifluoromethylalkynylation of unactivated alkenes is realized fr...
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| Published in | Journal of fluorine chemistry Vol. 267; pp. 110107 - 110112 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
LAUSANNE
Elsevier B.V
01.04.2023
Elsevier |
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| Abstract | •Terminal alkynes are used in trifluoromethylalkynylation of unactivated alkenes.•The design of copper/N,N,N-ligand catalyst ensures its success.•Mild conditions make it operationally simple.
A copper-catalyzed three-component radical trifluoromethylalkynylation of unactivated alkenes is realized from Togni-II reagent and readily available terminal alkynes under mild conditions to afford an array of β-trifluoromethylated alkynes. The utilization of a multidentate N,N,N-ligand is crucial for the efficient radical generation and the C(sp3)–C(sp) bond formation. Facile transformations of the difunctionalization products highlight its potential utility in the synthesis of various trifluoromethyl-containing building blocks.
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| AbstractList | •Terminal alkynes are used in trifluoromethylalkynylation of unactivated alkenes.•The design of copper/N,N,N-ligand catalyst ensures its success.•Mild conditions make it operationally simple.
A copper-catalyzed three-component radical trifluoromethylalkynylation of unactivated alkenes is realized from Togni-II reagent and readily available terminal alkynes under mild conditions to afford an array of β-trifluoromethylated alkynes. The utilization of a multidentate N,N,N-ligand is crucial for the efficient radical generation and the C(sp3)–C(sp) bond formation. Facile transformations of the difunctionalization products highlight its potential utility in the synthesis of various trifluoromethyl-containing building blocks.
[Display omitted] A copper-catalyzed three-component radical trifluoromethylalkynylation of unactivated alkenes is realized from Togni-II reagent and readily available terminal alkynes under mild conditions to afford an array of beta-tri- fluoromethylated alkynes. The utilization of a multidentate N,N,N-ligand is crucial for the efficient radical generation and the C(sp3)-C(sp) bond formation. Facile transformations of the difunctionalization products highlight its potential utility in the synthesis of various trifluoromethyl-containing building blocks. |
| ArticleNumber | 110107 |
| Author | Gu, Qiang-Shuai Liu, Xin-Yuan Li, Zhong-Liang Ren, Yang-Qing Yang, Chang-Jiang Liu, Lin |
| Author_xml | – sequence: 1 givenname: Yang-Qing surname: Ren fullname: Ren, Yang-Qing organization: School of Science and Institute of Scientific Research, Great Bay University, Dongguan 523000, China – sequence: 2 givenname: Chang-Jiang surname: Yang fullname: Yang, Chang-Jiang organization: School of Science and Institute of Scientific Research, Great Bay University, Dongguan 523000, China – sequence: 3 givenname: Zhong-Liang surname: Li fullname: Li, Zhong-Liang organization: Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China – sequence: 4 givenname: Qiang-Shuai surname: Gu fullname: Gu, Qiang-Shuai organization: Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China – sequence: 5 givenname: Lin surname: Liu fullname: Liu, Lin email: liul@gbu.edu.cn organization: School of Science and Institute of Scientific Research, Great Bay University, Dongguan 523000, China – sequence: 6 givenname: Xin-Yuan orcidid: 0000-0002-6978-6465 surname: Liu fullname: Liu, Xin-Yuan email: liuxy3@sustech.edu.cn organization: Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China |
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| Keywords | Unactivated alkenes Terminal alkyne Radical reaction Trifluoromethylalkynylation Copper STYRENES SILVER ELIMINATION 1,2-ADDITION ALKYNYLATION BROMIDES C-H BONDS IODIDES FLUORINE 1,2-DIFUNCTIONALIZATION |
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| Snippet | •Terminal alkynes are used in trifluoromethylalkynylation of unactivated alkenes.•The design of copper/N,N,N-ligand catalyst ensures its success.•Mild... A copper-catalyzed three-component radical trifluoromethylalkynylation of unactivated alkenes is realized from Togni-II reagent and readily available terminal... |
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| SubjectTerms | Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Copper Physical Sciences Radical reaction Science & Technology Terminal alkyne Trifluoromethylalkynylation Unactivated alkenes |
| Title | Copper-catalyzed radical trifluoromethylalkynylation of unactivated alkenes with terminal alkynes |
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