文章摘要
基于烯胺酮中间体 “一锅两步”法合成β-羰基砜衍生物
One-Pot Two Steps Synthesis of β-Keto-Sulfones via the Enaminone Intermediate
投稿时间:2019-06-26  修订日期:2019-08-24
DOI:
中文关键词: β-羰基砜  烯胺酮  三氯化铁/叔丁基过氧化氢  自由基加成
英文关键词: β-keto-sulfones  enaminone  FeCl3?6H2O/TBHP system  radical addition
基金项目:国家自然科学基金(51802096);湖南文理学院博士科研启动基金(No. 17BSQD32), 大学生创新创业研究项目(ZC1816)
作者单位E-mail
唐裕才 湖南文理学院 yctang1009@163.com 
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中文摘要:
      β-羰基砜是一类重要的含砜基官能团化合物,是一类重要的有机中间体。提供了一种新的基于酮α位sp3 C-H的自由基磺酰化反应合成β-羰基砜方法。反应分为两个步骤:首先将酮化合物转化为更加活泼的烯胺酮中间体,随后在FeCl3?6H2O/TBHP体系下发生自由基加成、氧化、亲核取代反应、脱去DMF得到最终产物。反应底物普适性好, 总体而言, 芳环上取代基为吸电子基团时比供电子基团表现出更高的反应活性。该方法具有操作简单、绿色环保等特点,为合成含β-羰基砜骨架分子结构提供了一种新途径。
英文摘要:
      β-keto-sulfones are an important sulfone-containing molecules and also serves as a versatile building blocks in organic synthsis. In this paper, we developed a novel method to construct various β-keto-sulfones that formed from the radical sulfonylation of carbonyl α-Csp3-H. The present method in-cluding two steps: firstly, the ketones react with DMF-DMA to generate more reactive enaminone inter-mediate, then with the assistance of FeCl3?6H2O/TBHP system, the enaminone intermediate underwent radical addition, oxidation, nucleophilic substitution and the loss of DMF would produce the β-keto-sulfones. This methodology will provide new strategies for construct β-keto-sulfone-type products, which has advantages of simple operation, mild reaction conditions and good functional group tolerance.
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