Yang Xiaobo, Liu Wenbo, Li Lu, Wei Wei, Li Chao-Jun
Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8, Canada.
Institute of Catalysis for Energy and Environment, College of Chemistry & Chemical Engineering, Shenyang Normal University, Shenyang, 110034, P. R. China.
Chemistry. 2016 Oct 17;22(43):15252-15256. doi: 10.1002/chem.201603608. Epub 2016 Sep 16.
Herein, we report a simple, redox-neutral and pH-neutral photo-induced carboiodination reaction under very mild conditions. This protocol employs readily available and cheap aryl bromides and sodium iodide as the starting materials to synthesize valuable functionalized dihydrobenzofurans and indolines in good to excellent yields with broad functional-group compatibility. As examples to demonstrate the utility of this protocol, gram-scale reactions and further transformations of the products were accomplished towards the synthesis of bioactive drug candidates. Most significantly, to the best of our knowledge, this reaction represents the first example of a cascade atom-radical-transfer addition involving the cleavage of aromatic C-Br bond.
在此，我们报道了一种在非常温和的条件下进行的简单、氧化还原中性和pH中性的光诱导碳碘化反应。该方法使用易于获得且廉价的芳基溴化物和碘化钠作为起始原料，以良好至优异的产率合成有价值的官能化二氢苯并呋喃和吲哚啉，且官能团兼容性广泛。作为证明该方法实用性的实例，实现了克级反应以及产物的进一步转化，以合成具有生物活性的候选药物。最重要的是，据我们所知，该反应代表了涉及芳族C-Br键断裂的级联原子自由基转移加成的首个实例。
