Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) Oxide
- 29 July 2000
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (17) , 5342-5349
- https://doi.org/10.1021/jo000679p
Abstract
Palladium-catalyzed cross-coupling of aryl- or alkenylsilanols, silanediols, and silanetriols with a variety of iodoarenes by the catalysis of palladium(0) and in the presence of silver(I) oxide furnished the coupling products in good to excellent yields. The reactions of silanediols or silanetriols under similar conditions proceeded much faster than those of silanols to afford the corresponding coupling products in excellent yields within shorter reaction periods (5−12 h). The measurement of the X-ray diffraction (XRD) pattern of the silver residue after the reaction revealed that silver(I) oxide was converted to silver(I) iodide.Keywords
This publication has 20 references indexed in Scilit:
- A Facile Preparation and Cyclopropanation of 1-AlkenylsilanolsBulletin of the Chemical Society of Japan, 1998
- Facile Preparation of Vicinal Allylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization ReactionBulletin of the Chemical Society of Japan, 1997
- Highly Efficient and Accelerated Suzuki Aryl Couplings Mediated by Phosphine-Free Palladium SourcesThe Journal of Organic Chemistry, 1994
- Substrate-directable chemical reactionsChemical Reviews, 1993
- Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromaticsChemical Reviews, 1990
- Alkenylfluorosilanes as widely applicable substrates for the palladium-catalyzed coupling of alkenylsilane/fluoride reagents with alkenyl iodidesThe Journal of Organic Chemistry, 1989
- Nickel- or palladium-catalyzed cross coupling. 31. Palladium- or nickel-catalyzed reactions of alkenylmetals with unsaturated organic halides as a selective route to arylated alkenes and conjugated dienes: scope, limitations, and mechanismJournal of the American Chemical Society, 1987
- NMR spectroscopic studies on chalcogen compounds. 4. Carbon-13 isotope effect on selenium-77 and tellurium-125 nuclear shielding and its correlation with carbon-selenium bond distances. Tellurium-123 isotope effect on tellurium-125 nuclear shieldingJournal of the American Chemical Society, 1982
- Epimerization of bicyclo[6.1.0.]nonatrieneJournal of the American Chemical Society, 1975
- Preparation of Some Organosilanediols and Phenylsilanetriol by Direct Hydrolysis Using Aniline as Hydrogen Chloride Acceptor1Journal of the American Chemical Society, 1959