Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane

• DOI: 10.3762/bjoc.13.209
• Publication Date: 2017-10-11T10:56:32Z
• Authors: James R Vyvyan; Courtney A Engles; Scott L Bray; Erik D Wold; Christopher L Porter; Mikhail O Konev
• Keywords: Hydrosilylation; Coupling reaction

Several Hiyama cross-coupling reactions of oxasilacycloalkenes and aryl iodides are described that produce trisubstituted Z-styrenes in moderate to excellent yields. Both electron-rich electron-poor tolerated the reaction. The oxasilacycloalkene coupling partners were prepared by ruthenium-catalyzed intramolecular anti-hydrosilylation alkynols. One products was converted a 1-benzoxocane, albeit low yield, using an Buchwald-Hartwig etherification. cyclic ether produced contains carbon skeleton heliannuol A.