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α-卤代酮的还原脱卤是有机合成中十分有用的转换反应.有机化学工作者对此已经开发了许多有效的方法,通常使用的有下列试剂和体系:三苯基膦、锌和醋酸体系、金属羰基化合物、碘化钠-三氧化硫-胺体系、碲氢化钠、二碘化钐等.钐试剂在有机合成中的应用近年来研究非常活跃.我们曾报道了α-卤代酮和醛在三碘化钐作用下偶联成α,β-不饱和酮的反应,这里我们报道的是把α-卤代酮加入SmI_3-THF溶液中,反应完成后用稀盐酸淬灭,结果得到α-卤代酮的还原脱卤产物(产率81—91%),反应式如下:
Reductive dehalogenation of α-halo ketones is a very useful conversion reaction in organic synthesis. Many effective methods have been developed by organic chemists for the following reagents and systems: triphenylphosphine, zinc and acetic acid Systems, metal carbonyls, sodium iodide-sulfur trioxide-amine systems, sodium telluride hydride, samarium diiodide, etc. The use of samarium reagents in organic synthesis has been very active in recent years.We have reported that α-halo ketones And aldehydes in the reaction of samarium triiodide into α, β-unsaturated ketone reaction, where we reported is the α-halo ketone was added SmI_3-THF solution, the reaction was quenched with dilute hydrochloric acid, the results The reduced dehalogenated product of the α-haloketone (yield 81-91%) was obtained according to the following reaction scheme: