Journal ArticleDOI
Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones
David R. M. Walton,F. Waugh +1 more
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In this paper, the silyl-substituted heterocycle (I) was constructed by using a mixture of acyl chloride-aluminium chloride and methylene chloride at 0-20°.About:
This article is published in Journal of Organometallic Chemistry.The article was published on 1972-04-01. It has received 176 citations till now. The article focuses on the topics: Friedel–Crafts reaction & Trimethylsilyl.read more
Citations
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Silylation as a protective method for terminal alkynes in oxidative couplings : A general synthesis of the parent polyynes H(CC)nH (n = 4–10, 12)☆
TL;DR: In this paper, the conditions established in a model coupling were used to obtain a chromatographically separable mixture of polynesians in the series H(CC)n (n = 4, 10, 12) by sequences involving Cu-catalysed oxidative couplings.
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New entry to a three-component pyrimidine synthesis by TMS-Ynones via Sonogashira coupling.
Alexei S. Karpov,Thomas Müller +1 more
TL;DR: This mild ynone synthesis is a suitable entry to 2,4-disubstituted pyrimidines in the sense of a one-pot three-component reaction, i.e., a coupling-addition-cyclocondensation sequence.
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Pd-catalyzed copper-free carbonylative Sonogashira reaction of aryl iodides with alkynes for the synthesis of alkynyl ketones and flavones by using water as a solvent.
TL;DR: The Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction to synthesize alkynyl ketones from terminal alkynes and aryl iodides was achieved by using water as a solvent and was successfully applied to the synthesis of flavones.
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Carbonylative Sonogashira Coupling of Terminal Alkynes with Aqueous Ammonia
TL;DR: Carbononylative coupling of phenylethyne with 4-methoxy-1-iodobenzene in the presence of 1 mol % PdCl(2)(PPh(3))(2), 2 equiv of 0.5 M aqueous ammonia, and CO gives the corresponding alpha,beta-alkynyl ketone in 72% isolated yield after stirring at room temperature for 41 h, while noncarbonylatives coupling product is not obtained.
References
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Copper(I) substitutions. Scope and mechanism of cuprous acetylide substitutions
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Substitutions- und Additionsreaktionen an silylierten Acetylenen
TL;DR: In mono-silylierten Acetylenen, z. B. im Trimethylsilyl-phenylacetylen, ist die Silygruppe ebenfalls gegen einen Acylrest austauschbar.
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The Preparation of Acetylenic Ketones Using Soluble Silver Acetylides
R. B. Davis,D. H. Scheiber +1 more
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The alkali cleavage of some (phenylethynyl)-silanes and -germanes
C. Eaborn,David R. M. Walton +1 more
TL;DR: In this paper, the rates of cleavage by aqueous methanolic alkali of some (XC 6 H 4 ) 3 SiCCPh compounds, and also of some YC 6H 4 CCMR 3 compounds in which M Si or Ge.