Shaikh, Rizwan S. and Duesel, Simon J. S. and Koenig, Burkhard (2016) Visible-Light Photo-Arbuzov Reaction of Aryl Bromides and Trialkyl Phosphites Yielding Aryl Phosphonates. ACS CATALYSIS, 6 (12). pp. 8410-8414. ISSN 2155-5435,
Full text not available from this repository. (Request a copy)Abstract
Aryl phosphonates are functional groups frequently found in pharmaceutical and crop protection agents. For their synthesis via C-P bond formation typically transition-metal-catalyzed reactions are used. We report a visible-light photo-Arbuzov reaction as an efficient, mild, and metal-free alternative. Rhodamine 6G (Rh.6G) is used as the photocatalyst, generating aryl radicals under blue light. Coupling of the radicals with a wide range of trivalent phosphites gives aryl phosphonates in good to very good isolated yields. The mild reaction conditions allow the introduction of a phosphonate group into complex and sensitive pharmaceutically active molecules such as benzodiazepams and nicergoline by the activation of a carbon halogen bond.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | P BOND FORMATION; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; H-PHOSPHONATE; ROOM-TEMPERATURE; METAL-COMPLEXES; PHOTOCATALYSIS; ARYLATION; CATALYSIS; HALIDES; rhodamine 6G; phosphonate; photo-Arbuzov; visible light; C-P bond formation |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 04 Apr 2019 11:15 |
| Last Modified: | 04 Apr 2019 11:15 |
| URI: | https://pred.uni-regensburg.de/id/eprint/3866 |
Actions (login required)
 |
View Item |
