Vyvyan James R, Engles Courtney A, Bray Scott L, Wold Erik D, Porter Christopher L, Konev Mikhail O
Department of Chemistry, Western Washington University, 516 High Street, Bellingham, WA 98225, USA.
Beilstein J Org Chem. 2017 Oct 11;13:2122-2127. doi: 10.3762/bjoc.13.209. eCollection 2017.
Several Hiyama cross-coupling reactions of oxasilacycloalkenes and aryl iodides are described that produce trisubstituted -styrenes in moderate to excellent yields. Both electron-rich and electron-poor aryl iodides are tolerated in the cross-coupling reaction. The oxasilacycloalkene coupling partners were prepared by ruthenium-catalyzed intramolecular anti-hydrosilylation of alkynols. One of the cross-coupling products was converted to a 1-benzoxocane, albeit in low yield, using an intramolecular Buchwald-Hartwig etherification. The cyclic ether produced contains the carbon skeleton of heliannuol A.
描述了几种硅杂环烯烃与芳基碘的日山交叉偶联反应，这些反应能以中等至优异的产率生成三取代苯乙烯。富电子和贫电子的芳基碘在交叉偶联反应中均能耐受。硅杂环烯烃偶联伙伴是通过钌催化的炔醇分子内反式硅氢化反应制备的。其中一种交叉偶联产物通过分子内布赫瓦尔德-哈特维希醚化反应转化为1-苯并氧杂环辛烷，尽管产率较低。所生成的环状醚含有向日葵醇A的碳骨架。
