Water-controlled selective preparation of α-mono or α,α′-dihalo ketones via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin
Water-controlled selective preparation of α-mono or α,α′-dihalo ketones via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin
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DOI：
10.1039/c7gc00283a
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发表时间：
2017-04
期刊：
影响因子：
9.8
通讯作者：
Chao Wu;Xiu Xin;Zhimin Fu;Long-Yong Xie;Kaijian Liu;Z. Wang;Wenyi Li;Zhi-Hui Yuan;Wei-Min He
中科院分区：
文献类型：
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作者：
Chao Wu;Xiu Xin;Zhimin Fu;Long-Yong Xie;Kaijian Liu;Z. Wang;Wenyi Li;Zhi-Hui Yuan;Wei-Min He
在有机合成中，控制从同一起始原料生成多个产物的反应是一个极具吸引力和挑战性的概念。提出了一种水控三组分硫脲催化未活化炔、1，3-二卤代-5，5-二甲基海因和水的级联反应选择性合成α-单卤酮或α，α‘-二卤酮的方法。在45℃的丙酮水溶液中合成了α-单卤酮，在室温下以纯水为唯一溶剂生成了α，α‘-二卤酮。
The control of a reaction that can produce multiple products from the same starting material is a highly attractive and challenging concept in organic synthesis. An efficient protocol for the selective synthesis of α-mono or α,α′-dihalo ketones via a water-controlled three-component thiourea-catalyzed cascade reaction of unactivated alkynes, 1,3-dihalo-5,5-dimethylhydantoin and water has been developed. α-Monohaloketones were obtained in aqueous acetone at 45 °C; conversely, α,α′-dihalo ketones were formed with pure water as the sole solvent at room temperature.