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Nickel-Catalyzed Regio- and Stereoselective Silylation of Terminal Alkenes with Silacyclobutanes: Facile Access to Vinylsilanes from Alkenes
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Abstract
Treatment of terminal alkenes with silacyclobutanes under nickel catalysis resulted in silylation of the alkenes and yielded the corresponding vinylsilanes in a highly regio- and stereoselective fashion. The reaction provides a facile access to vinylsilanes starting from trivial terminal alkenes as well as styrenes, 1,3-dienes, and acrylate esters.
Citing Articles
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
Palladium-Catalyzed Enantioselective Desymmetrization of Silacyclobutanes: Construction of Silacycles Possessing a Tetraorganosilicon Stereocenter
Ryo Shintani, Kohei Moriya, and Tamio HayashiJournal of the American Chemical Society2011 133 (41), 16440-16443Palladium-Catalyzed Enantioselective Desymmetrization of Silacyclobutanes: Construction of Silacycles Possessing a Tetraorganosilicon Stereocenter
Ryo Shintani, Kohei Moriya, and Tamio HayashiJournal of the American Chemical Society2011 133 (41), 16440-16443A palladium-catalyzed desymmetrization of alkyne-tethered silacyclobutanes to give silacycles possessing a tetraorganosilicon stereocenter has been developed, and high chemo- and enantioselectivities have been achieved by the use of a newly synthesized ...
Palladium- and Nickel-Catalyzed Carbon−Carbon Bond Insertion Reactions with Alkylidenesilacyclopropanes
Kay M. Buchner and K. A. WoerpelOrganometallics2010 29 (7), 1661-1669Palladium- and Nickel-Catalyzed Carbon−Carbon Bond Insertion Reactions with Alkylidenesilacyclopropanes
Kay M. Buchner and K. A. WoerpelOrganometallics2010 29 (7), 1661-1669Palladium and nickel catalysts promoted highly selective carbon−carbon bond insertion reactions with di-tert-butyl-alkylidenesilacyclopropanes. Pd(PPh3)4 was demonstrated to be the optimal catalyst, allowing for a variety of carbon−carbon π-bond insertion ...
Iridium-Catalyzed (Z)-Trialkylsilylation of Terminal Olefins
Biao Lu and J. R. FalckThe Journal of Organic Chemistry2010 75 (5), 1701-1705Iridium-Catalyzed (Z)-Trialkylsilylation of Terminal Olefins
Biao Lu and J. R. FalckThe Journal of Organic Chemistry2010 75 (5), 1701-1705A complex of commercial [Ir(OMe)(cod)]2 and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrative silylation of terminal alkenes, but not 1,2-disubstituted alkenes, with triethylsilane or benzyldimethylsilane in THF at 40 °C. ...
New Strategies for Protecting Group Chemistry: Synthesis, Reactivity, and Indirect Oxidative Cleavage of para-Siletanylbenzyl Ethers
Sami F. Tlais, Hubert Lam, Sarah E. House and Gregory B. DudleyThe Journal of Organic Chemistry2009 74 (5), 1876-1885New Strategies for Protecting Group Chemistry: Synthesis, Reactivity, and Indirect Oxidative Cleavage of para-Siletanylbenzyl Ethers
Sami F. Tlais, Hubert Lam, Sarah E. House and Gregory B. DudleyThe Journal of Organic Chemistry2009 74 (5), 1876-1885Reported herein is a new entry in the growing arsenal of arylmethyl ether protecting groups. The para-siletanylbenzyl (PSB) ether is electronically similar to the benzyl ether. Cleavage of the PSB ether is accomplished under mild conditions
involving ...
Palladium-Catalyzed Formal Cycloaddition of Silacyclobutanes with Enones: Synthesis of Eight-Membered Cyclic Silyl Enolates
Koji Hirano, Hideki Yorimitsu and Koichiro OshimaOrganic Letters2008 10 (11), 2199-2201Palladium-Catalyzed Formal Cycloaddition of Silacyclobutanes with Enones: Synthesis of Eight-Membered Cyclic Silyl Enolates
Koji Hirano, Hideki Yorimitsu and Koichiro OshimaOrganic Letters2008 10 (11), 2199-2201Treatment of silacyclobutanes with enones under palladium catalysis resulted in formal cycloaddition to yield the corresponding eight-membered ring. The reaction provides a facile and convergent access to synthetically useful eight-membered cyclic silyl ...
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History
- Published In Issue May 16, 2007
- Received February 9, 2007
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