Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis
An efficient tertiary alkylation reaction of olefins with 1,3-dicarbonyl compounds was developed by virtue of copper catalyst without the use of expensive ligands or additives. In contrast to alkyl Heck-type reaction, alkyl halide is not required. Notably, by varying the nitrogen and air atmosphere,...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2021
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| Online Access: | https://hdl.handle.net/10356/147446 |
| _version_ | 1811689048569282560 |
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| author | Tian, Ming-Qing Wang, Cong Hu, Xu-Hong Loh, Teck-Peng |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Tian, Ming-Qing Wang, Cong Hu, Xu-Hong Loh, Teck-Peng |
| author_sort | Tian, Ming-Qing |
| collection | NTU |
| description | An efficient tertiary alkylation reaction of olefins with 1,3-dicarbonyl compounds was developed by virtue of copper catalyst without the use of expensive ligands or additives. In contrast to alkyl Heck-type reaction, alkyl halide is not required. Notably, by varying the nitrogen and air atmosphere, the reaction selectively produces alkylation and alkylation-oxygenation products, respectively. Initial investigations revealed that an α-carbonyl alkyl radical species might be involved in the process. |
| first_indexed | 2024-10-01T05:41:54Z |
| format | Journal Article |
| id | ntu-10356/147446 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:41:54Z |
| publishDate | 2021 |
| record_format | dspace |
| spelling | ntu-10356/1474462021-04-01T08:14:27Z Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis Tian, Ming-Qing Wang, Cong Hu, Xu-Hong Loh, Teck-Peng School of Physical and Mathematical Sciences Science::Chemistry Heck-type Alkenylation Bond Functionalization An efficient tertiary alkylation reaction of olefins with 1,3-dicarbonyl compounds was developed by virtue of copper catalyst without the use of expensive ligands or additives. In contrast to alkyl Heck-type reaction, alkyl halide is not required. Notably, by varying the nitrogen and air atmosphere, the reaction selectively produces alkylation and alkylation-oxygenation products, respectively. Initial investigations revealed that an α-carbonyl alkyl radical species might be involved in the process. We thank the National Natural Science Foundation of China (21702106), the Natural Science Foundation of Jiangsu Province (BK20170967), and the Start-up Grant from Nanjing Tech University (39839101 and 39837101) for financial support. The SICAM Fellowship by Jiangsu National Synergetic Innovation Center for Advanced Materials is also acknowledged. 2021-04-01T08:14:27Z 2021-04-01T08:14:27Z 2019 Journal Article Tian, M., Wang, C., Hu, X. & Loh, T. (2019). Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis. Organic Letters, 21(6), 1607-1611. https://dx.doi.org/10.1021/acs.orglett.9b00142 1523-7060 0000-0001-6584-2901 0000-0002-2936-337X https://hdl.handle.net/10356/147446 10.1021/acs.orglett.9b00142 30793908 2-s2.0-85062351469 6 21 1607 1611 en Organic Letters © 2019 American Chemical Society. All rights reserved. |
| spellingShingle | Science::Chemistry Heck-type Alkenylation Bond Functionalization Tian, Ming-Qing Wang, Cong Hu, Xu-Hong Loh, Teck-Peng Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis |
| title | Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis |
| title_full | Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis |
| title_fullStr | Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis |
| title_full_unstemmed | Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis |
| title_short | Divergent C-H oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis |
| title_sort | divergent c h oxidative radical functionalization of olefins to install tertiary alkyl motifs enabled by copper catalysis |
| topic | Science::Chemistry Heck-type Alkenylation Bond Functionalization |
| url | https://hdl.handle.net/10356/147446 |
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