42972-67-8

Upstream product

• 3034-05-7 6-chloroflavanone 
• 73220-39-0 6-chloro-3-iodo-4H-chromen-4-one 
• 603-33-8 triphenylbismuthane 
• 536-74-3 phenylacetylene 
• 635-93-8 5-chlorosalicyclaldehyde 
• 98-09-9 benzenesulfonyl chloride 
• 73220-32-3 C₁₁H₁₂ClNO₂ 
• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 
• 85980-21-8 (dimethyl)(phenyl)sulfonium trifluoromethanesulfonate 
• 960-16-7 tributylphenylstannane 
• 73220-38-9 3-bromo-6-chloro-4H-1-benzopyran-4-one 
• 73220-32-3 (2E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)-2-propen-1-one 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 66003-76-7 Diphenyliodonium triflate 

Relevant academic research and scientific papers

Arylation of ortho-Hydroxyarylenaminones by Sulfonium Salts and Arenesulfonyl Chlorides: An Access to Isoflavones

Herein we disclose three new methods for the straightforward and efficient synthesis of 3-arylchromones following the arylation of ortho-hydroxyarylenaminones by vast diversities of bench-stable and easy-to-use sulfonium salts and arenesulfonyl chlorides.

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation

This paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylala

Visible-light-mediated arylation of: Ortho -hydroxyarylenaminones: Direct access to isoflavones

In this work we highlight two new methods for the synthesis of isoflavones through consecutive domino arylation of ortho-hydroxyarylenaminones with in situ photogenerated aryl radicals. As precursors for aryl radicals we used aryl onium reagents such as diazonium and diaryliodonium salts. Notably, the photo-Meerwein arylation by aryl diazonium tetrafluoroborates demonstrated high efficiency in terms of yields and can be considered as a method of choice for the straightforward assembly of 3-aryl-substituted chromones. Ultimately, 26 compounds were prepared in good to excellent yields using the developed synthetic protocols.

Pd-Catalyzed efficient cross-couplings of 3-iodochromones with triarylbismuths as substoichiometric multicoupling organometallic nucleophiles

An efficient cross-coupling of 3-iodochromones with triarylbismuths under catalytic palladium conditions is reported. Triarylbismuths were employed as substoichiometric multicoupling nucleophiles for the synthesis of a variety of substituted isoflavones.

Hypervalent Iodine Oxidation of Flawanones: Convenient and Useful Syntheses of Flavones and IsoFlavones

Hypervalent iodine oxidation of flavanones (1a-g) under a variety of conditions, offering convenient and valuable routes to the syntheses of flavones (2a-g) and isoflavones (3a-g), is described.The course of these oxidation reactions is greatly influenced by the reaction conditions and it is possible to select appropriate conditions for following a desired route (2/3).The mechanistic rationale for these transformations is also discussed.

Ligand Coupling Route to Isoflavanones and Isoflavones

Phenylation of 3-phenylsulfonylchroman-4-ones using Ph3BiCO3 leading to the synthesis of isoflavanones and isoflavones is reported.

Oxidation of Flavanones using Thallium(III) Salts: A New Route for the Synthesis of Flavones and Isoflavones

When treated with thallium(III) acetate in acetic acid or acetonitrile, flavanones undergo facile dehydrogenation to afford flavones whereas, upon treatment with thallium(III) toluene-p-sulfonate or thallium(III) nitrate in propionitrile or acetonitrile, respectively, they undergo oxidative 2,3-aryl migration to give isoflavones in high yield.

Oxidative 1,2-aryl rearrangement in flavanones using thallium(III) p-tolylsulphonate (TTS): A new useful route to isoflavones

Oxidation of flavanones using thallium(III) p-tolylsulphonate (prepared in situ by the reaction of thallium(III) acetate and p-toluene sulphonic acid) in propionitrile leads to 1,2-aryl shift providing a new useful route to the synthesis of isoflavones.

Novel Synthesis of Isoflavones by the Palladium-Catalyzed Cross-Coupling Reaction of 3-Bromochromones with Arylboronic Acids or Its Esters

The synthesis of isoflavone derivatives by means of palladium-catalyzed cross-coupling reaction between 3-bromochromones and arylboronic acids or its butyl esters is described.