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

Autor: James R. Vyvyan, Courtney A. Engles, Scott L. Bray, Erik D. Wold, Christopher L. Porter, Mikhail O. Konev
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 13, Iss 1, Pp 2122-2127 (2017)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.13.209
Popis: 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 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.
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