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Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters
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| Zeitschriftentitel: | Angewandte Chemie |
|---|---|
| Personen und Körperschaften: | , , , |
| In: | Angewandte Chemie, 132, 2020, 22, S. 8580-8584 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
|
| Schlagwörter: |
| author_facet |
Fasano, Valerio Winter, Nils Noble, Adam Aggarwal, Varinder K. Fasano, Valerio Winter, Nils Noble, Adam Aggarwal, Varinder K. |
|---|---|
| author |
Fasano, Valerio Winter, Nils Noble, Adam Aggarwal, Varinder K. |
| spellingShingle |
Fasano, Valerio Winter, Nils Noble, Adam Aggarwal, Varinder K. Angewandte Chemie Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters General Medicine |
| author_sort |
fasano, valerio |
| spelling |
Fasano, Valerio Winter, Nils Noble, Adam Aggarwal, Varinder K. 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.202002246 <jats:title>Abstract</jats:title><jats:p>There is considerable interest in incorporating fluorine into agrochemicals and pharmaceuticals to improve their biological properties. Whilst a number of methods have been reported for installing CH<jats:sub>2</jats:sub>F and CHF<jats:sub>2</jats:sub> groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α‐fluoro‐boronic esters. These unique intermediates can be readily transformed into the corresponding mono‐ or difluoromethylated compounds through proto‐ or fluorodeboronation, respectively. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2‐migration over competing decomposition of the carbanion. DFT calculations informed and supported the experimental findings.</jats:p> Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters Angewandte Chemie |
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| title |
Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_unstemmed |
Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_full |
Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_fullStr |
Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_full_unstemmed |
Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_short |
Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_sort |
divergent, stereospecific mono‐ and difluoromethylation of boronic esters |
| topic |
General Medicine |
| url |
http://dx.doi.org/10.1002/ange.202002246 |
| publishDate |
2020 |
| physical |
8580-8584 |
| description |
<jats:title>Abstract</jats:title><jats:p>There is considerable interest in incorporating fluorine into agrochemicals and pharmaceuticals to improve their biological properties. Whilst a number of methods have been reported for installing CH<jats:sub>2</jats:sub>F and CHF<jats:sub>2</jats:sub> groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α‐fluoro‐boronic esters. These unique intermediates can be readily transformed into the corresponding mono‐ or difluoromethylated compounds through proto‐ or fluorodeboronation, respectively. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2‐migration over competing decomposition of the carbanion. DFT calculations informed and supported the experimental findings.</jats:p> |
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| author | Fasano, Valerio, Winter, Nils, Noble, Adam, Aggarwal, Varinder K. |
| author_facet | Fasano, Valerio, Winter, Nils, Noble, Adam, Aggarwal, Varinder K., Fasano, Valerio, Winter, Nils, Noble, Adam, Aggarwal, Varinder K. |
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| description | <jats:title>Abstract</jats:title><jats:p>There is considerable interest in incorporating fluorine into agrochemicals and pharmaceuticals to improve their biological properties. Whilst a number of methods have been reported for installing CH<jats:sub>2</jats:sub>F and CHF<jats:sub>2</jats:sub> groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α‐fluoro‐boronic esters. These unique intermediates can be readily transformed into the corresponding mono‐ or difluoromethylated compounds through proto‐ or fluorodeboronation, respectively. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2‐migration over competing decomposition of the carbanion. DFT calculations informed and supported the experimental findings.</jats:p> |
| doi_str_mv | 10.1002/ange.202002246 |
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| imprint | Wiley, 2020 |
| imprint_str_mv | Wiley, 2020 |
| institution | DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Rs1, DE-Pl11, DE-105, DE-14, DE-Ch1 |
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| physical | 8580-8584 |
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| publishDateSort | 2020 |
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| series | Angewandte Chemie |
| source_id | 49 |
| spelling | Fasano, Valerio Winter, Nils Noble, Adam Aggarwal, Varinder K. 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.202002246 <jats:title>Abstract</jats:title><jats:p>There is considerable interest in incorporating fluorine into agrochemicals and pharmaceuticals to improve their biological properties. Whilst a number of methods have been reported for installing CH<jats:sub>2</jats:sub>F and CHF<jats:sub>2</jats:sub> groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α‐fluoro‐boronic esters. These unique intermediates can be readily transformed into the corresponding mono‐ or difluoromethylated compounds through proto‐ or fluorodeboronation, respectively. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2‐migration over competing decomposition of the carbanion. DFT calculations informed and supported the experimental findings.</jats:p> Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters Angewandte Chemie |
| spellingShingle | Fasano, Valerio, Winter, Nils, Noble, Adam, Aggarwal, Varinder K., Angewandte Chemie, Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters, General Medicine |
| title | Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_full | Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_fullStr | Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_full_unstemmed | Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_short | Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| title_sort | divergent, stereospecific mono‐ and difluoromethylation of boronic esters |
| title_unstemmed | Divergent, Stereospecific Mono‐ and Difluoromethylation of Boronic Esters |
| topic | General Medicine |
| url | http://dx.doi.org/10.1002/ange.202002246 |