Copper-catalyzed 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters via radical relay/1,5-hydrogen-atom transfer
The trifunctionalization of alkenes has emerged as a versatile strategy for the efficient construction of diverse structural units and complex molecules in synthetic chemistry. Herein, we describe a novel 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters through simultaneous...
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| Published in | ORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 24; pp. 6096 - 6102 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
05.12.2023
Royal Society of Chemistry |
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| Abstract | The trifunctionalization of alkenes has emerged as a versatile strategy for the efficient construction of diverse structural units and complex molecules in synthetic chemistry. Herein, we describe a novel 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters through simultaneous construction of four C-C bonds and a C=N bond in one pot based on the radical relay/1,5-hydrogen-atom transfer (HAT) processes under a mild copper catalytic system. The resulting reaction of spirocyclic derivatives displays high chemical selectivity, broad substrate scope, as well as high atom- and step-economy. Preliminary control experiments and density functional theory (DFT) calculations reveal sequential functionalizations and cyclizations in this transformation. |
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| AbstractList | The trifunctionalization of alkenes has emerged as a versatile strategy for the efficient construction of diverse structural units and complex molecules in synthetic chemistry. Herein, we describe a novel 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters through simultaneous construction of four C-C bonds and a C=N bond in one pot based on the radical relay/1,5-hydrogen-atom transfer (HAT) processes under a mild copper catalytic system. The resulting reaction of spirocyclic derivatives displays high chemical selectivity, broad substrate scope, as well as high atom- and step-economy. Preliminary control experiments and density functional theory (DFT) calculations reveal sequential functionalizations and cyclizations in this transformation. The trifunctionalization of alkenes has emerged as a versatile strategy for the efficient construction of diverse structural units and complex molecules in synthetic chemistry. Herein, we describe a novel 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters through simultaneous construction of four C–C bonds and a C≡N bond in one pot based on the radical relay/1,5-hydrogen-atom transfer (HAT) processes under a mild copper catalytic system. The resulting reaction of spirocyclic derivatives displays high chemical selectivity, broad substrate scope, as well as high atom- and step-economy. Preliminary control experiments and density functional theory (DFT) calculations reveal sequential functionalizations and cyclizations in this transformation. |
| Author | Wei, Wen-Ting Jiang, Li-Lin Zhou, Yu Yang, Wen-Hui Qiu, Hui Wang, Ling-Tao Deng, Chao |
| Author_xml | – sequence: 1 givenname: Li-Lin surname: Jiang fullname: Jiang, Li-Lin organization: Ningbo Univ, Sch Mat Sci & Chem Engn, Ningbo 315211, Zhejiang, Peoples R China – sequence: 2 givenname: Hui surname: Qiu fullname: Qiu, Hui organization: Ningbo Univ, Sch Mat Sci & Chem Engn, Ningbo 315211, Zhejiang, Peoples R China – sequence: 3 givenname: Yu surname: Zhou fullname: Zhou, Yu organization: Ningbo Univ, Sch Mat Sci & Chem Engn, Ningbo 315211, Zhejiang, Peoples R China – sequence: 4 givenname: Ling-Tao surname: Wang fullname: Wang, Ling-Tao organization: Ningbo Univ, Sch Mat Sci & Chem Engn, Ningbo 315211, Zhejiang, Peoples R China – sequence: 5 givenname: Wen-Hui surname: Yang fullname: Yang, Wen-Hui organization: Ningbo Univ, Sch Mat Sci & Chem Engn, Ningbo 315211, Zhejiang, Peoples R China – sequence: 6 givenname: Chao surname: Deng fullname: Deng, Chao email: chaodeng@njau.edu.cn organization: Nanjing Agr Univ, Coll Sci, Dept Chem, Jiangsu Key Lab Pesticide Sci, Nanjing 210095, Peoples R China – sequence: 7 givenname: Wen-Ting orcidid: 0000-0001-7942-8656 surname: Wei fullname: Wei, Wen-Ting email: weiwenting@nbu.edu.cn organization: Ningbo Univ, Sch Mat Sci & Chem Engn, Ningbo 315211, Zhejiang, Peoples R China |
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| CitedBy_id | crossref_primary_10_3390_molecules29020458 crossref_primary_10_1021_acs_orglett_4c00981 crossref_primary_10_1039_D4OB01810A crossref_primary_10_1002_adsc_202400116 crossref_primary_10_1039_D4QO00995A |
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| Keywords | FUNCTIONALIZATION ATOM-TRANSFER ALKENES CASCADE TRIFUNCTIONALIZATION CYCLIZATION |
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| Snippet | The trifunctionalization of alkenes has emerged as a versatile strategy for the efficient construction of diverse structural units and complex molecules in... |
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| SubjectTerms | Alkenes Chemistry Chemistry, Organic Copper Covalent bonds Density functional theory Esters Hydrogen atoms Organic chemistry Oxime esters Physical Sciences Radicals Relay Science & Technology Substrates |
| Title | Copper-catalyzed 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters via radical relay/1,5-hydrogen-atom transfer |
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