Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones
The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C[BOND]C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration;...
| Main Authors: | , |
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| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/107166 http://hdl.handle.net/10220/25414 |
| _version_ | 1826121915599683584 |
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| author | Tnay, Ya Lin Chiba, Shunsuke |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Tnay, Ya Lin Chiba, Shunsuke |
| author_sort | Tnay, Ya Lin |
| collection | NTU |
| description | The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C[BOND]C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones. |
| first_indexed | 2024-10-01T05:39:59Z |
| format | Journal Article |
| id | ntu-10356/107166 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:39:59Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1071662021-11-02T16:16:14Z Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones Tnay, Ya Lin Chiba, Shunsuke School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Physical chemistry::Catalysis The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C[BOND]C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones. 2015-04-17T01:47:42Z 2019-12-06T22:25:56Z 2015-04-17T01:47:42Z 2019-12-06T22:25:56Z 2015 2015 Journal Article Tnay, Y. L., & Chiba, S. (2015). Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones. Chemistry - an Asian journal, 10(4), 873-877. 1861-4728 https://hdl.handle.net/10356/107166 http://hdl.handle.net/10220/25414 10.1002/asia.201403196 en Chemistry - an Asian journal © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Physical chemistry::Catalysis Tnay, Ya Lin Chiba, Shunsuke Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones |
| title | Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones |
| title_full | Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones |
| title_fullStr | Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones |
| title_full_unstemmed | Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones |
| title_short | Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones |
| title_sort | copper catalyzed aerobic c c bond cleavage of lactols with n hydroxy phthalimide for synthesis of lactones |
| topic | DRNTU::Science::Chemistry::Physical chemistry::Catalysis |
| url | https://hdl.handle.net/10356/107166 http://hdl.handle.net/10220/25414 |
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