Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp2)-H Bonds with Elemental Selenium in Air
Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp2)-H Bonds with Elemental Selenium in Air
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DOI：
10.1021/acs.orglett.7b00116
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发表时间：
2017-03-03
期刊：
影响因子：
5.2
通讯作者：
Nishihara, Yasushi
中科院分区：
文献类型：
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作者：
Iwasaki, Masayuki;Miki, Natsumi;Nishihara, Yasushi
镍催化的带有8-喹啉基助剂的苯甲酰胺与元素硒的直接硒化通过在有氧条件下形成碳硒和氮-硒键以良好的产率提供苯并异硒唑酮。除了芳基C-H键之外，该方法还可以应用于烯基C-H键，构建异硒唑酮骨架。简单的机理分析表明，该反应是通过一个速率决定C-H键断裂进行的。所得苯并异硒唑酮转化为各种有机硒化合物，并用作烯酸溴代内酯化反应的催化剂。
Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-H bonds, the method can also be applied to alkenyl C-H bonds, constructing an isoselenazolone skeleton. Simple mechanistic analysis shows that the reaction proceeds through a rate-determining C-H bond cleavage. The obtained benzoisoselenazolones are transformed into various organoselenium compounds and utilized as the catalyst for bromolactonization of alkenoic acids.