Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui’s radical susceptibilities support the obtained results.
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| Main Authors: | , , , , , , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Language: | English |
| Published: |
American Chemical Society
2021-08-06
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| Subjects: | Hydrocarbons, Addition reactions, Oxygen, Chemical reactions, Selectivity, |
| Online Access: | http://hdl.handle.net/10261/246803 http://dx.doi.org/10.13039/501100011033 |
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| Summary: | A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui’s radical susceptibilities support the obtained results. |
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