24017-08-1

Upstream product

• 3199-83-5 1,2-epoxy-1-phenyl-indan 
• 913192-84-4 phenyl[2-[(trimethylsilanyl)ethynyl]phenyl]methanol 
• 108-86-1 bromobenzene 
• 83-33-0 inden-1-one 
• 958-79-2 1,3-dibromo-1,3-diphenylpropan-2-one 
• 7108-64-7 Dimethyl-oxo-sulfonium 
• 1871-76-7 diphenylacetic acid chloride 
• 117-34-0 2,2-diphenylacetic acid 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 1610735-41-5 1-((benzyloxy)(phenyl)methyl)-2-ethynylbenzene 
• 1610735-40-4 1-((allyloxy)(phenyl)methyl)-2-ethynylbenzene 
• 1610735-39-1 1-ethynyl-2-(methoxy(phenyl)methyl)benzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1610735-38-0 1-(ethoxy(phenyl)methyl)-2-ethynylbenzene 

Downstream Products

• 36255-55-7 1-Phenyl-1-(2-propenyl)-2-indanon 
• 36255-53-5 5-Phenyl-6,7-dihydro-5H-benzocycloheptene 
• 92724-33-9 1-hydroxy-1-phenyl-1,3-dihydro-2H-inden-2-one 
• 32889-71-7 3-hydroxy-3-phenyl-1,2 indiandione 
• 55190-65-3 cis/trans-5,6-Diphenyl-sym-dibenzocyclooctan 
• 55190-64-2 1-phenyl-1,2-dihydrobenzocyclobutene 
• 713-36-0 2-benzyltoluene 
• 144176-43-2 1-Phenylindan-2-one phenylhydrazone 
• 36255-45-5 1-(3,3-Dimethoxypropyl)-1-phenyl-2-indanon 
• 144176-38-5 5,6-Dihydro-6-phenylindeno<2,1-b>-indole 

Relevant academic research and scientific papers

Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α-carbonyl sulfoxonium ylides onto benzenes, benzofurans and N-p-toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and N-methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.

Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant

Oxygenation of alkenes is one of the most straightforward routes for the construction of carbonyl compounds. Wacker oxidation provides a broadly useful strategy to convert the mineral oil into higher value-added carbonyl chemicals. However, the conventional Wacker chemistry remains problematic, such as the poor activity for internal alkenes, the lack of anti-Markovnikov regioselectivity, and the high cost and chemical waste resulted from noble metal catalysts and stoichiometric oxidant. Here, we describe an unprecedented dehydrogenative oxygenation of β-alkyl styrenes and their derivatives with water under external-oxidant-free conditions by utilizing the synergistic effect of photocatalysis and proton-reduction catalysis that can address these challenges. This dual catalytic system possesses the single anti-Markovnikov selectivity due to the property of the visible-light-induced alkene radical cation intermediate.

Oxone-acetone mediated Wacker-type oxidation of benzo-fused olefins

Herein we disclose a novel application of the oxone-acetone combination for the Wacker-type oxidation of indenes and dihydronaphthalenes leading, respectively, to indan-2-ones and 2-tetralones. The amount of the base employed in the reaction seems to switch the reaction path from dioxygenation to Wacker-type oxidation. Control experiments suggest that the reaction is not proceeding via the epoxide route and also that there is no role of trace amounts of metals present in the reagents on the current oxidation.

OXONE-ACETONE MEDIATED METAL FREE PREPARATION OF SYN-DIOLS

The present invention disclose a simple and high yielding process of Oxone-acetone mediated metal free syn-dihydroxylation of benzo fused olefins of formula (II) to obtain library of dioxolo compounds of formula (I). The invention further disclsoe a simple and high yielding process of Oxone-acetone mediated metal free syn-dihydroxylation of stilbene and its derivatives of formula (III) thereof. Also disclosed herein is Wacker-type oxidation of benzo-fused olefins of formula (X). The invention further disclose compounds of formula (I) which can be useful for the treatment of HIV, cancer or malaria.

Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 2-indanones chemoselectively: Effects of ligands and solvents

The selective syntheses of 1- and 2-indan-one compounds from 2-ethynylbenzyl ethers have been achieved with suitable catalysts and solvents. The highly acidic [tris(pentafluorophenyl)phos-phine]gold hexafluoroantimonate [(C6F5)3AuSbF6] in nitromethane (MeNO2) preferably gives 1-indan-ones whereas [(ortho-biphenyl) di(tert-butyl)phosphine] gold triflimide [(tBu)2(o-biphenyl) AuNTf2] in dichloroethane tends to form 2-indanone derivatives. For 2-indanone products, we isolated two indenyl methyl ethers for deuterium labeling analyses, providing evidence for p-alkyne activation.

Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones

Striking gold: A series of variously functionalized propynyl arenes was smoothly converted into indan-2-ones by a new gold(I)-catalyzed oxidative cyclization process. [LAu]NTf2 (Tf=trifluoromethanesulfonyl) is a superior catalyst both in terms of yield and kinetics for the present transformation. Copyright

[3,3]-sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: Synthesis of substituted 2-indanones and indenes

Substituted benzyl alkynyl ethers, prepared from the corresponding α-alkoxy ketones in a two-step sequence involving enol triflate formation and KOtBu-induced E2 elimination, undergo [3,3]-sigmatropic rearrangement/ intramolecular 5-exo-dig cyclization at 60 °C to form substituted 2-indanones in good overall yields. 1,3-cis-Disubstituted-2-indanones are formed preferentially when the benzylic substituent R1 is bulky. Substituted indenes may be prepared from 2-indanones in high yields by Horner-Wadsworth-Emmons reaction.

Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers

(Chemical Equation Presented) α-Alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R2 = allyl) furnishes instead γ,δ-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at -78 °C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R2 = benzyl) rearranges to indanone 7 upon heating to 60 °C.

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Dynamic kinetic resolution-asymmetric transfer hydrogenation of 1-aryl-substituted cyclic ketones

A range of 1-aryl-2-tetranols, and 1-phenyl-2-indanol, have been generated in high yield and enantiomeric excess from the corresponding racemic ketones, via a dynamic kinetic resolution-transfer hydrogenation process, using Ru(II)-TsDPEN in formic acid/triethylamine (5:2). This provides a potential entry to an asymmetric total synthesis of benzazepines such as Sch 39166.