Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions
A photoinduced esterification reaction has been developed. In this reaction, benzylsilane shows very nice reactivity and selectivity, affording the corresponding esters as the only products. Under photo irradiation, the highly active bromo radical can be generated from the pre-catalyst CBr4, which w...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2017-02-01
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| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610316300758 |
| _version_ | 1828390500206379008 |
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| author | Aishun Ding Ruixia Xie Guangxin Gu Jing Sun |
| author_facet | Aishun Ding Ruixia Xie Guangxin Gu Jing Sun |
| author_sort | Aishun Ding |
| collection | DOAJ |
| description | A photoinduced esterification reaction has been developed. In this reaction, benzylsilane shows very nice reactivity and selectivity, affording the corresponding esters as the only products. Under photo irradiation, the highly active bromo radical can be generated from the pre-catalyst CBr4, which would promote the initial CSi bond cleavage of benzylsilane via single electron transfer and the final transformation of acetal into ester via proton transfer. The existence of oxygen can not only oxidize the in situ generated benzyl radical into aldehyde intermediate, but also assist to regenerate bromo radical from bromine anion. |
| first_indexed | 2024-12-10T06:46:36Z |
| format | Article |
| id | doaj.art-a0b0da429e084a3abb6c1100d5059764 |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-12-10T06:46:36Z |
| publishDate | 2017-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-a0b0da429e084a3abb6c1100d50597642022-12-22T01:58:39ZengElsevierJournal of Saudi Chemical Society1319-61032017-02-0121224524910.1016/j.jscs.2016.10.001Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditionsAishun Ding0Ruixia Xie1Guangxin Gu2Jing Sun3Department of Macromolecular Science, Fudan University, 220 Handan Road, Shanghai 200433, PR ChinaSchool of Chemistry and Materials Science, Liaoning Shihua University, Dandong Road 1, Fushun 113001, PR ChinaDepartment of Materials Science, Fudan University, 220 Handan Road, Shanghai 200433, PR ChinaSchool of Chemistry and Materials Science, Liaoning Shihua University, Dandong Road 1, Fushun 113001, PR ChinaA photoinduced esterification reaction has been developed. In this reaction, benzylsilane shows very nice reactivity and selectivity, affording the corresponding esters as the only products. Under photo irradiation, the highly active bromo radical can be generated from the pre-catalyst CBr4, which would promote the initial CSi bond cleavage of benzylsilane via single electron transfer and the final transformation of acetal into ester via proton transfer. The existence of oxygen can not only oxidize the in situ generated benzyl radical into aldehyde intermediate, but also assist to regenerate bromo radical from bromine anion.http://www.sciencedirect.com/science/article/pii/S1319610316300758PhotochemistryEsterificationBromoBenzylsilaneEster |
| spellingShingle | Aishun Ding Ruixia Xie Guangxin Gu Jing Sun Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions Journal of Saudi Chemical Society Photochemistry Esterification Bromo Benzylsilane Ester |
| title | Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions |
| title_full | Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions |
| title_fullStr | Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions |
| title_full_unstemmed | Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions |
| title_short | Bromo-catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions |
| title_sort | bromo catalyzed photo esterification of benzylsilanes with alcohols under aerobic conditions |
| topic | Photochemistry Esterification Bromo Benzylsilane Ester |
| url | http://www.sciencedirect.com/science/article/pii/S1319610316300758 |
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