17791-25-2

Upstream product

• 1074-12-0 phenylglyoxal hydrate 
• 2628-17-3 4-Vinylphenol 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 37559-18-5 3-phenylprop-2-ynyl acetate 
• 108-95-2 phenol 
• 66894-71-1 3-Hydroperoxy-1-phenylpropin-⁽¹⁾ 
• 20426-12-4 (E)-3-(4-hydroxyphenyl)-1-phenyl-2-propen-1-one 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 38239-55-3 4-hydroxychalcone 
• 768-03-6 Phenyl vinyl ketone 
• 5440-69-7 N-isopropylbenzamide 
• 2628-16-2 p-acetoxystyrene 

Downstream Products

• 1413765-50-0 4-hydroperoxy-4-(3-oxo-3-phenylpropyl)cyclohexa-2,5-dien-1-one 
• 39534-17-3 4-hydroxy-4-(3-oxo-3-phenylpropyl)cyclohexa-2,5-dien-1-one 
• 197915-35-8 3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-phenyl-5,6-dihydro-pyran-2-one 
• 207736-95-6 4-hydroxy-6-[2-(4-hydroxy-phenyl)ethyl]-6-phenyl-5,6-dihydro-pyran-2-one 
• 95465-74-0 4-(3-oxo-3-phenylpropyl)phenyl acetate 

Relevant academic research and scientific papers

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

Ketone Synthesis by Direct, Orthogonal Chemoselective Hydroacylation of Alkenes with Amides: Use of Alkenes as Surrogates of Alkyl Carbanions

Direct functionalization of alkenes and direct transformation of carboxamides are two exciting areas that have attracted considerable attention in recent years. We report herein that secondary amides, the least reactive derivatives of carbonyl compounds, upon activated with triflic anhydride, can serve as effective hydroacylating reagents in partner with alkenes to yield ketones at ambient temperature. The method was applied to the one-step synthesis of racemic dihydro-ar-turmerone. In this method, alkenes serve as surrogates of organometallic reagents, which allows the orthogonal chemoselective reactions. The ready availability of many olefins such as camphene and norbornene permits one-step ketone synthesis that would require several steps by conventional methods.

Organocatalyzed biomimetic selective reduction of c=c double bonds of chalcones

In this article, we reported a biomimetic approach for chemoselective reduction of C=C double bonds in chalcones under metal and acid free conditions, that relies on olefin activation by hydrogen bond formation. The process requires only catalytic amount of ephedrine as hydrogen bond donor and utilizes Hantzsch esters for transfer hydrogenation.

Decarboxylative Csp3-Csp3 coupling for benzylation of unstable ketone enolates: Synthesis of: P -(acylethyl)phenols

A new decarboxylative Csp3-Csp3 coupling approach for the benzylation of ketone enolates has been developed. A variety of raspberry ketone derivatives were conveniently synthesized in good to excellent yields under mild conditions. A crossover reaction shed light on the mechanism of this tandem reaction.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Unveiling the reactivity of propargylic hydroperoxides under gold catalysis

Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ke

Total synthesis of natural p -quinol cochinchinenone

Cochinchinenone has been synthesized in only five steps and four pots and in 58% overall yield from commercially available 2,3-dimethoxy-4-hydroxy- benzaldehyde and OPMB-protected p-hydroxy acetophenone, the key step being the oxone-mediated oxidative dea

Electrophilic chemistry of propargylic alcohols in imidazolium ionic liquids: Propargylation of arenes and synthesis of propargylic ethers catalyzed by metallic triflates [Bi(OTf)3, Sc(OTf)3, Yb(OTf) 3], TfOH, or B(C6F5)3

Metallic triflates M(OTf)3 (M = Bi, Sc, Yb), immobilized in imidazolium ionic liquids [BMIM][BF4], [BMIM][PF6] and [BMIM][OTf] are efficient systems for one-pot reactions of propargylic alcohols 1,3-diphenyl-2-propyn-1-ol Ia, 1-methyl-3-phenyl-2-propyn-1-ol Ib, and 2-pentyn-1-ol Ic, with a wide range of arenes bearing activating substituents, under mild conditions. The [BMIM][PF6]/B(C6F 5)3 and [BMIM][PF6]/TfOH systems were superior in propargylation with Ib and Ic, while reaction of 3-phenyl-2-propyn-1-ol Id with activated aromatics resulted in the formation of diaryl-propanones instead. Propargylation of anisole with Ib under M(OTf)3 catalysis is highly para selective, but with TfOH or B(C6F5)3 as catalyst the ortho isomer was also formed. Steric influence of the propargylic moiety on substrate selectivity is reflected in the lack of ortho propargylation for phenol and ethylbenzene by using propargylic alcohol Ia, and notable formation of the ortho isomer employing alcohol Ib. In the later case para selectivity could be increased by running the reaction at r. t. for 10 h. The Bi(OTf)3-catalyzed reaction of 1,3-dimethoxybenzene with Ia led to minor formation of dipropargylated derivative, along with the monopropargyl product. Propargylation of the less reactive arenes (mesitylene, ethylbenzene, toluene), using Sc(OTf)3 as catalyst, led increasingly to the formation of dipropargylic ethers and propargyl ketones, with no ring propargylation product with toluene. Concomitant formation of dipropargylic ether was also observed in Yb(OTf)3-catalyzed propargylation of β-naphthol, whereas propargylation of 2-nitro and 4-nitro-aniline led to N-propargylation. The recycling/reuse of the IL was demonstrated in representative cases with no appreciable decrease in the conversions over 3 cycles. It was also shown that recycled IL could be used to propargylate a different aromatic compound. The efficacy of IL/M(OTf)3 and IL/TfOH systems for cross-breeding two propargylic alcohols or a propargylic alcohol with a non-propargylic alcohol and/or self-coupling, to form a wide variety of functionalized ethers is also demonstrated.

AMBERLYST-15 CATALYZED ADDITION OF PHENOLS TO α,β-UNSATURATED KETONES

Amberlyst-15 has been used to catalyze regioselective additions of phenols to α,β-unsaturated ketones in yields of 20-90percent.The reaction is superior to the analogous reaction employing concentrated sulfuric acid in affording greater yields and purer products with a minimum of laboratory operations.