Preparation of Vinyl Silyl Ethers and Disiloxanes via the Silyl-Heck Reaction of Silyl Ditriflates
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چکیده
منابع مشابه
Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.
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Using rational ligand design, we have developed of a second-generation ligand, bis(3,5-di-tert-butylphenyl)(tert-butyl)phosphine, for the preparation of allylsilanes using the palladium-catalyzed silyl-Heck reaction. This new ligand provides nearly complete suppression of starting material alkene isomerization that was observed with our first-generation catalyst, providing vastly improved yield...
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In the silyl Lewis acid-promoted Mukaiyama aldol reaction, the steric and electronic properties of the silyl group on the silyl Lewis acid influence the reaction mechanism and product distribution. When super silyl triflates such as (TMS)3SiOTf and (TES)3SiOTf are used as Lewis acids, the silyl group of the silyl enol ether chemoselectively transfers to the product. The mechanistic details have...
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Five-membered carbocyclic rings appear in all classes of organic materials including pharmaceutical agents, polymers, natural products, and catalysts. Accordingly, their preparation has challenged synthetic chemists since the inception of the field. In this regard, [3+2] cycloadditions—both concerted and stepwise—represent convergent strategies for the formation of the cyclopentane nucleus. Dip...
متن کامل1-Phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers
1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol (2) has been synthesized and investigated as a new bis-annelation reagent for silyl enol ethers. Reagent 2 can be synthesized by a Grignard reaction of vinyl magnesium bromide with 3-phenylthiocyclohexenone. The reaction with silyl enol ethers takes place under Lewis acid catalysis and generally proceeds in good yields. The resulting phenylthiodienes can ...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2013
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja407748z