Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy
Abstract Stereocontrolled construction of tetrasubstituted olefins has been an attractive issue yet remains challenging for synthetic chemists. In this manuscript, alkynyl selenides, when treated with ArBCl2, are subject to an exclusive 1,1-carboboration, affording tetrasubstituted alkenes with exce...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-56184-3 |
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| author | Xuan Di Sitian Zhou Yali Qin Wenjun Li Yue Zhang Jie Zhang Xu Shen Jie Han Jin Xie Hongming Jin |
| author_facet | Xuan Di Sitian Zhou Yali Qin Wenjun Li Yue Zhang Jie Zhang Xu Shen Jie Han Jin Xie Hongming Jin |
| author_sort | Xuan Di |
| collection | DOAJ |
| description | Abstract Stereocontrolled construction of tetrasubstituted olefins has been an attractive issue yet remains challenging for synthetic chemists. In this manuscript, alkynyl selenides, when treated with ArBCl2, are subject to an exclusive 1,1-carboboration, affording tetrasubstituted alkenes with excellent levels of E-selectivity. Detailed mechanistic studies, supported by DFT calculations, elucidates the role of selenium in this 1,1-addition process. Coupled with subsequent C-B and C-Se bond transformations, this 1,1-addition protocol constitutes a modular access to stereodefined all-carbon tetrasubstituted alkenes. The merit of this approach is demonstrated by programmed assembly of diverse functionalized multi-arylated alkenes, especially enabling the stereospecific synthesis of all six possible stereoisomers of tetraarylethene (TAE) derived from the random permutation of four distinct aryl substituents around the double bond. The diversity-oriented synthesis is further utilized to explore different TAE luminogenic properties and potential Se-containing antitumor lead compounds. |
| format | Article |
| id | doaj-art-f2ddfdc05d3e4c4d8c54dd503f994234 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-f2ddfdc05d3e4c4d8c54dd503f9942342025-01-26T12:41:45ZengNature PortfolioNature Communications2041-17232025-01-0116111210.1038/s41467-025-56184-3Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategyXuan Di0Sitian Zhou1Yali Qin2Wenjun Li3Yue Zhang4Jie Zhang5Xu Shen6Jie Han7Jin Xie8Hongming Jin9School of Pharmacy, Nanjing University of Chinese MedicineState Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing UniversitySchool of Pharmacy, Nanjing University of Chinese MedicineJiangsu Key Laboratory of Drug Target Research and Drug Discovery of Neurodegenerative Disease, School of Medicine, Nanjing University of Chinese MedicineJiangsu Key Laboratory of Drug Target Research and Drug Discovery of Neurodegenerative Disease, School of Medicine, Nanjing University of Chinese MedicineSchool of Pharmacy, Nanjing University of Chinese MedicineJiangsu Key Laboratory of Drug Target Research and Drug Discovery of Neurodegenerative Disease, School of Medicine, Nanjing University of Chinese MedicineState Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing UniversityState Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing UniversitySchool of Pharmacy, Nanjing University of Chinese MedicineAbstract Stereocontrolled construction of tetrasubstituted olefins has been an attractive issue yet remains challenging for synthetic chemists. In this manuscript, alkynyl selenides, when treated with ArBCl2, are subject to an exclusive 1,1-carboboration, affording tetrasubstituted alkenes with excellent levels of E-selectivity. Detailed mechanistic studies, supported by DFT calculations, elucidates the role of selenium in this 1,1-addition process. Coupled with subsequent C-B and C-Se bond transformations, this 1,1-addition protocol constitutes a modular access to stereodefined all-carbon tetrasubstituted alkenes. The merit of this approach is demonstrated by programmed assembly of diverse functionalized multi-arylated alkenes, especially enabling the stereospecific synthesis of all six possible stereoisomers of tetraarylethene (TAE) derived from the random permutation of four distinct aryl substituents around the double bond. The diversity-oriented synthesis is further utilized to explore different TAE luminogenic properties and potential Se-containing antitumor lead compounds.https://doi.org/10.1038/s41467-025-56184-3 |
| spellingShingle | Xuan Di Sitian Zhou Yali Qin Wenjun Li Yue Zhang Jie Zhang Xu Shen Jie Han Jin Xie Hongming Jin Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy Nature Communications |
| title | Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy |
| title_full | Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy |
| title_fullStr | Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy |
| title_full_unstemmed | Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy |
| title_short | Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy |
| title_sort | diversity oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem addition strategy |
| url | https://doi.org/10.1038/s41467-025-56184-3 |
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