Kanishchev Oleksandr S, Dolbier William R
Department of Chemistry, PO Box 117200, University of Florida, Gainesville, FL, 32611-7200, USA.
Chemistry. 2017 Jun 7;23(32):7677-7681. doi: 10.1002/chem.201701627. Epub 2017 May 15.
Metallaphotoredox cross-coupling reactions have recently emerged as a powerful tool for the construction of C(sp )-C(sp ) 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 -Sulfoxaflor.
金属光氧化还原交叉偶联反应最近已成为构建烷基链与芳族体系（包括缺电子杂芳基）之间C(sp)-C(sp)键的有力工具，而缺电子杂芳基是已知具有挑战性的偶联伙伴。在本文中，我们报道了镍/铱催化的、容易获得的S-取代硫代乳酸与缺电子杂芳基溴的光氧化还原脱羧偶联反应，该反应生成了带有烷基硫醚侧链的简单但难以通过其他方法获得的杂芳烃。为了证明这种偶联反应的实际用途，我们展示了其在一步合成最近上市的杀虫剂氟啶虫胺腈的关键中间体以及用于短路线合成SF-氟啶虫胺腈中的效率。
