85662-85-7

Upstream product

• 362-86-7 3-(4-fluorophenyl)-3-phenylpropanoic acid 
• 462-06-6 fluorobenzene 
• 102-92-1 cinnamoyl chloride 
• 620964-91-2 3-(4-fluorophenyl)-1H-inden-1-one 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 71-43-2 benzene 
• 2142-69-0 2-bromophenyl methyl ketone 
• 1608-51-1 4-fluorochalcone 
• 6630-33-7 ortho-bromobenzaldehyde 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 5908-41-8 benzoyltrimethylsilane 
• 130995-12-9 1-(4-fluorophenyl)-2-trimethylsilylacetylene 
• 1765-93-1 4-fluoroboronic acid 
• 87694-37-9 4-methyl-N'-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)benzenesulfonohydrazide 

Downstream Products

• 80272-55-5 cis-3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-ol 
• 104087-10-7 1-chloro-4-(4-flurophenyl)indan 
• 80273-08-1 Lu 17-123 
• 1422961-06-5 (S)-3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one 
• 85721-01-3 (1R,3R)-3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-ol 

Relevant academic research and scientific papers

Palladium-catalyzed asymmetric reductive Heck reaction of aryl halides

Asymmetric reductive Heck reaction of aryl halides is realized in high stereoselectivity. Hydrogen-bond donors, trialkylammonium salts in a glycol solvent, were used to promote halide dissociation from neutral arylpalladium complexes to access cationic, stereoselective pathways.

Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre

The marine transaminase, P-ω-TA, can be employed for the transamination from 1-aminotetralins and 1-aminoindanes with differentiation of stereochemistry at both the site of reaction and at a remote stereocentre resulting in formation of ketone products with up to 93% ee. While 4-substituents are tolerated on the tetralin core, the presence of 3- or 8-substituents is not tolerated by the transaminase. In general P-ω-TA shows capacity for remote diastereoselectivity, although both the stereoselectivity and efficiency are dependent on the specific substrate structure. Optimum efficiency and selectivity are seen with 4-haloaryl-1-aminotetralins and 3-haloaryl-1-aminoindanes, which may be associated with the marine origin of this enzyme. This journal is

Palladium Nanoparticles-Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction

An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2′-iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2′-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. (Figure presented.).

Synthesis of 3-aryl-1-indanones via CsF-promoted coupling of arylboronic acids with N-tosylhydrazones

A series of 17 3-aryl-1-indanones, four of which are novel, were prepared in good yield via a CsF-promoted reductive cross-coupling of the monotosylhydrazone of a 1,3-indanedione with an arylboronic acid. The method demonstrates wide substrate scope and good functional group tolerance. Moreover, the 3-aryl-1-indanones could also be prepared on a multi-gram scale.

Gold(I)-Catalyzed Addition of Silylacetylenes to Acylsilanes: Synthesis of Indanones by C-H Functionalization through a Gold(I) Carbenoid

A gold(I)-catalyzed synthesis of indanones from trimethylsilylacetylenes and acylsilanes is presented. The reaction is initiated through a synergistic acylsilane activation-gold acetylide formation and involves consecutive alkyne σ-gold(I) addition, π-activation, and 1,2-migration of a silyl group. Studies performed on the reaction mechanism allowed to establish the nature of the silyl migrating group and invoke the participation of a gold(I) carbenoid intermediate. The reaction is completed by a gold(I) C-H functionalization step.

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.

Gold-catalyzed oxidative cyclizations of cis-3-En-1-ynes to form cyclopentenone derivatives

Golden tendencies: The title reaction for synthesizing cyclopentenone derivatives utilizes a gold complex and 8-methylquinoline oxide as the catalyst system (see scheme; IPr=1,3-bis(diisopropylphenyl)imidazol-2-ylidene). Such products are not attainable using diazocarbonyl reagents, as the gold carbenoids tend to react with C-H bonds. Copyright

BTISA-catalyzed Friedel-Crafts bimolecular cyclization of cinnamic acid under superelectrophilic solvation conditions

Friedel-Crafts bimolecular cyclizations of cinnamic acid and cinnamoyl chloride with aromatic compounds in strong and superstrong acids in present of 1 mol% BTISA were investigated. It was demonstrated that catalytic amounts of this new superacid have essential effect on such type of reactions. Its use makes possible the preparation of indanones with quantitative yields.

Versatile synthesis of 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones

We have developed a novel and versatile synthesis of racemic 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones. This method is especially attractive because it avoids strong acidic conditions and consequently a larger number of sensitive functional groups are accepted during synthesis compared with existing methods.

Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles

The chemistry of cinnamic acids and related compounds has been studied. In superacid-catalyzed reactions with arenes, two competing reaction mechanisms are proposed. Both mechanisms involve the formation of dicationic intermediates (superelectrophiles), and the reactions can lead to either chalcone-type products or indanone products. The direct observation of a dicationic species (by low-temperature 13C NMR) is reported. We provide clear evidence that protonated carboxylic acid groups (or the corresponding acyl cation) can enhance the reactivity of an adjacent electrophilic center. Triflic acid is also found to be an effective acid catalyst for the direct synthesis of some electron-deficient chalcones and heterocyclic chalcones from cinnnamic acids.