at Google ScholarTitle data
Zhang, Yu ; Han, Xinyu ; Li, Dong ; Wang, Dinggang ; Wang, Jinxin ; Luan, Xin ; Ni, Shao-Fei ; Das, Shoubhik ; Zhang, Wei-Dong:
Facile Access to Hindered Ethers via Photoinduced O–H Bond Insertions.
In: ACS Central Science.
(2025)
.
ISSN 2374-7951
DOI: https://doi.org/10.1021/acscentsci.5c00099
Abstract in another language
The synthesis of the hindered and polyfluorinated dialkyl ethers poses challenges owing to the bulkiness of tertiary alcohols and the low nucleophilicity of polyfluorinated alcohols. Additionally, associated competitive side reactions always provide poor reactivities. Although certain strategies, such as electrocatalytic decarboxylation and hydroalkoxylation, have been explored, a straightforward method for obtaining ethers with structural diversity remains elusive. In this study, we have exploited the photoinduced approach that involves the in situ formation of singlet carbenes followed by O–H insertions to access the hindered and polyfluorinated ethers with congested or polyfluorinated alcohols. Moreover, other nucleophiles such as phenols, H2O, thiols, silanols, tributyltin hydride, etc., are also tolerable to obtain valuable products. The gram-scale synthesis of marketed drugs and the modification of complex molecules demonstrate the practicality of this approach. The detailed mechanistic studies have elucidated the key intermediates and reaction mechanism, which were distinct from traditional metal-carbenoid O–H insertions.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit - Univ.-Prof. Dr. Shoubhik Das |
| Result of work at the UBT: | Yes |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 24 Apr 2025 05:46 |
| Last Modified: | 24 Apr 2025 05:46 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93349 |