Ni/Ir-Catalyzed Photoredox Decarboxylative Coupling of S-Substituted Thiolactic Acids with Heteroaryl Bromides: Short Synthesis of Sulfoxaflor and Its SF 5 Analog.
| Autor: | Kanishchev OS; Department of Chemistry, PO Box 117200, University of Florida, Gainesville, FL, 32611-7200, USA., Dolbier WR Jr; Department of Chemistry, PO Box 117200, University of Florida, Gainesville, FL, 32611-7200, USA. |
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| Jazyk: | angličtina |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2017 Jun 07; Vol. 23 (32), pp. 7677-7681. Date of Electronic Publication: 2017 May 15. |
| DOI: | 10.1002/chem.201701627 |
| Abstrakt: | Metallaphotoredox cross-coupling reactions have recently emerged as a powerful tool for the construction of C(sp 2 )-C(sp 3 ) bonds between alkyl chains and aromatic systems, including electron-deficient heteroaryls, which are known to be challenging coupling partners. In this article, we disclose the Ni/Ir-catalyzed photoredox decarboxylative coupling of readily available S-substituted thiolactic acids with electron-deficient heteroaryl bromides, which resulted in the formation of simple but otherwise not easily accessible heteroarenes with alkylsulfide side chains. To demonstrate a practical use of this coupling reaction, we have shown its efficiency in the one-step synthesis of a key intermediate in the synthesis of the recently marketed insecticide Sulfoxaflor, and for the short synthesis of SF (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.) |
| Databáze: | MEDLINE |
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