- Preparation and reaction chemistry of novel silicon-substituted 1,3-dienes
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2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions.
- Choudhury, Partha P.,Welker, Mark E.
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p. 16892 - 16907
(2015/12/01)
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- A ruthenium-based catalytic system with switchable selectivity between cyclotrimerization and enyne metathesis/Diels-Alder reactions of terminal alkynes
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In this study, we report a practical catalytic system, [RuCl 2(p-cymene)]2/IPr (IPr: 1,3-bis(2,6 diisopropylphenyl) imidazol-2-ylidene), that can switch between cyclotrimerization and cross enyne metathesis. The cyclotrimerization reaction of phenylacetylene catalyzed by [RuCl2(p-cymene)]2 can be switched to enyne metathesis by the introduction of a sterically hindered N-heterocyclic carbene. The 1,3-diene formed during this reaction reacts with dienophiles to form the Diels-Alder adduct. A practical one-pot synthesis method, utilizing enyne metathesis/Diels-Alder reactions, was used to construct cyclic compounds in an efficient manner.
- Karabulut, Solmaz,Sariaslan, Begüm,?ztürk, Bengi ?zgün
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- Preparation and Diels-Alder/cross coupling reactions of new 2-boron-substituted 1,3-dienes
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Several new 2-boron substituted dienes have been prepared and characterized. Their reactivity in Diels- Alder reactions has been examined and the boron substituted cycloadducts of those cycloaddition reactions have been used in cross coupling reactions. One-pot tandem Diels-Alder/ cross coupling reactions of 2-boron substituted dienes are then also reported along with some experimental evidence that these one-pot reactions are proceeding through a Pd(II)-catalyzed Diels-Alder/cross coupling reaction pathway.
- Wang, Liqiong,Welker, Mark E.
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p. 8280 - 8286,7
(2020/10/15)
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- Preparation of 2-silicon-substituted 1,3-dienes and their diels-alder/cross-coupling reactions
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(Chemical Equation Presented) 2-Triethoxysilyl-substituted 1,3-butadiene has been prepared in 30-g quantities from chloroprene via a simple synthetic procedure. Silatrane- and catechol-substituted analogues of this main group element substituted diene wer
- Pidaparthi, Ramakrishna R.,Junker, Christopher S.,Welker, Mark E.,Day, Cynthia S.,Wright, Marcus W.
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supporting information; experimental part
p. 8290 - 8297
(2010/02/17)
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- Preparation and Diels-Alder/cross coupling reactions of a 2-diethanolaminoboron-substituted 1,3-diene
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A 2-diethanolamine boronyl substituted 1,3-diene has been synthesized in high yield and characterized spectroscopically as well as by X-ray crystallography. This diene has then subsequently been used in a number of fast, high yielding Diels-Alder/cross co
- Wang, Liqiong,Day, Cynthia S.,Wright, Marcus W.,Welker, Mark E.
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supporting information; experimental part
(2010/04/22)
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- COMPOUNDS AND COMPOSITIONS CONTAINING SILICON AND/OR OTHER HETEROATOMS AND/OR METALS AND METHODS OF MAKING AND USING THEM
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The present invention relates to compounds, intermediates, compositions, and methods of making compounds and intermediates related to the compounds of Formula (I) and/or Formula (II) and/or Formula (III) and/or Formula (IV) and/or Formula (VI) and/or Formula (VII) as disclosed herein wherein the various substituents are as defined in the written description.
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Page/Page column 30-31
(2008/12/05)
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