Cationic palladium complex-catalyzed cyclization-hydrosilylation of 1-alkene-6,11-diyne derivatives: Facile cyclization at the enyne part than at the diyne counterpart

A palladium complex, [(eta(3)-C3H5)Pd(cod)](+)[PF6](-) (C), catalyzes hydrosilylation of 1-dodecene-6,11-diyne (5) or 1-tridecene-6,11-diyne (7), and of their 9-oxo congeners (9 or 11), with HSiCl3 to form regioisomeric cyclization products (6, 8, 10, and 12, respectively), which arise between the d...

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Bibliographic Details
Published inChemistry letters Vol. 35; no. 8; pp. 846 - 847
Main Authors Shimamoto, Takamitsu, Hirano, Tomohiro, Nishimoto, Hiroyuki, Yamamoto, Keiji
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.08.2006
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CYCLIZATION/HYDROSILYLATION
SILYLATIVE CYCLIZATION
RHODIUM
1,6-HEPTADIYNE
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Summary:A palladium complex, [(eta(3)-C3H5)Pd(cod)](+)[PF6](-) (C), catalyzes hydrosilylation of 1-dodecene-6,11-diyne (5) or 1-tridecene-6,11-diyne (7), and of their 9-oxo congeners (9 or 11), with HSiCl3 to form regioisomeric cyclization products (6, 8, 10, and 12, respectively), which arise between the diyne part (path a) to form A series or between the enyne counterpart (path b) to form B series. The formation of product B is markedly favored with 1-tridecene-6,1 I-diyne derivatives as compared with 1-dodecene-6,11-diyne ones that possess a terminal alkyne.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2006.846