Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer
The generation of α-carbon radicals from alkoxyl radicals is challenging because 1,2-hydrogen atom transfer (HAT) is usually less favoured than 1,5-HAT. Here, the authors report a strategy to inhibit 1,5-HAT by introducing a silyl group into the α-position of alkoxyl radicals, enabling preparation o...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2021-04-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-021-22382-y |
| _version_ | 1818842744149245952 |
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| author | Zhaoliang Yang Yunhong Niu Xiaoqian He Suo Chen Shanshan Liu Zhengyu Li Xiang Chen Yunxiao Zhang Yu Lan Xiao Shen |
| author_facet | Zhaoliang Yang Yunhong Niu Xiaoqian He Suo Chen Shanshan Liu Zhengyu Li Xiang Chen Yunxiao Zhang Yu Lan Xiao Shen |
| author_sort | Zhaoliang Yang |
| collection | DOAJ |
| description | The generation of α-carbon radicals from alkoxyl radicals is challenging because 1,2-hydrogen atom transfer (HAT) is usually less favoured than 1,5-HAT. Here, the authors report a strategy to inhibit 1,5-HAT by introducing a silyl group into the α-position of alkoxyl radicals, enabling preparation of α-alkoxylimino alcohols and α-heteroaryl alcohols. |
| first_indexed | 2024-12-19T04:46:50Z |
| format | Article |
| id | doaj.art-6c1a3b2d619d43439e674cec1a34b3bd |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-12-19T04:46:50Z |
| publishDate | 2021-04-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-6c1a3b2d619d43439e674cec1a34b3bd2022-12-21T20:35:27ZengNature PortfolioNature Communications2041-17232021-04-011211910.1038/s41467-021-22382-yTuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transferZhaoliang Yang0Yunhong Niu1Xiaoqian He2Suo Chen3Shanshan Liu4Zhengyu Li5Xiang Chen6Yunxiao Zhang7Yu Lan8Xiao Shen9The Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversityThe Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversitySchool of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing UniversityThe Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversityThe Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversityThe Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversityThe Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversityThe Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversitySchool of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing UniversityThe Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds and Materials, Ministry of Education, Wuhan UniversityThe generation of α-carbon radicals from alkoxyl radicals is challenging because 1,2-hydrogen atom transfer (HAT) is usually less favoured than 1,5-HAT. Here, the authors report a strategy to inhibit 1,5-HAT by introducing a silyl group into the α-position of alkoxyl radicals, enabling preparation of α-alkoxylimino alcohols and α-heteroaryl alcohols.https://doi.org/10.1038/s41467-021-22382-y |
| spellingShingle | Zhaoliang Yang Yunhong Niu Xiaoqian He Suo Chen Shanshan Liu Zhengyu Li Xiang Chen Yunxiao Zhang Yu Lan Xiao Shen Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer Nature Communications |
| title | Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer |
| title_full | Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer |
| title_fullStr | Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer |
| title_full_unstemmed | Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer |
| title_short | Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer |
| title_sort | tuning the reactivity of alkoxyl radicals from 1 5 hydrogen atom transfer to 1 2 silyl transfer |
| url | https://doi.org/10.1038/s41467-021-22382-y |
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