10408-73-8

Upstream product

• 917-64-6 methyl magnesium iodide 
• 83-12-5 phenindione 
• 4767-56-0 (Z)-3-benzylidenephthalide 
• 673-32-5 1-Phenylprop-1-yne 
• 26260-02-6 2-iodobenzaldehyde 
• 86108-39-6 2-Methyl-2,3-diphenyl-3-(toluene-4-sulfonyloxy)-propionic acid ethyl ester 
• 6630-33-7 ortho-bromobenzaldehyde 
• 201230-82-2 carbon monoxide 
• 71-43-2 benzene 
• 4387-36-4 2-iodobenzonitrile 
• 138642-62-3 2-Cyanophenylboronic acid 
• 374538-03-1 2-methoxycarbonylphenylboronic acid 
• 1221067-99-7 methyl 4-(2-bromophenyl)-2-methylene-4-oxo-3-phenylbutanoate 
• 1221068-02-5 methyl 4-(2-bromophenyl)-2-methyl-4-oxo-3-phenylbut-2-enoate 

Relevant academic research and scientific papers

Rhodium-catalyzed annulation reactions of 2-cyanophenylboronic acid with alkynes and strained alkenes

(Chemical Equation Presented) A new [3 + 2] annulation reaction was developed in which 2-cyanophenylboronic acid reacted as a three-carbon component with alkynes or alkenes to afford substituted indenones or indanones. The use of an alkynoate even produced benzotropone, a formal [3 + 2 + 2] adduct. The cyclic skeletons were constructed by intramolecular nucleophilic addition of an intermediate organorhodium(I) species to a cyano group.

Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids

Palladlum(II) catalyzes annulation of internal alkynes with methyl 2-boronobenzoate and (2-boronophenyl)acetate to provide 2,3-disubstituted indenones and 3,4-disubstituted 2-naphthols, respectively. The annulation reaction would proceed through transmeta

Synthesis of Indenones Via Palladium-Catalyzed Carbonylation with Mo(CO)6 as a CO Surrogate

Transition-metal-catalyzed carbonylation of alkynes has emerged as a powerful engine for the synthesis of indenone compounds. Herein, we reported the development of an effective Pd-catalyzed ligand-free carbonylation of o-bromoaryl iodides with alkynes to afford indenone compounds. A broad range of functional groups on o-bromoaryl iodides and alkynes were tolerated in this protocol, giving carbonylation products. Furthermore, considering the factors of safety and operability, Mo(CO)6 was introduced into the reaction as a carbonyl source. Mechanistic investigations suggested that the reaction proceeded through sequential oxidative addition, alkyne insertion, carbonyl insertion, and reductive elimination steps to produce the observed carbonylation indenone products. Moreover, the indenones obtained with Mo(CO)6 as a CO surrogate can be functionalized to form synthetic useful derivatives via an environmentally friendly way.

Synthesis of indenones through rhodium(III)-catalyzed [3+2] annulation utilizing a recyclable carbazolyl leaving group

The rhodium(III)-catalyzed annulative coupling of 9-ben-zoylcarbazoles with internal alkynes proceeds efficiently through ortho CH and CN bond cleavages. This reaction provides direct access to variously substituted indanone derivatives. The carbazolyl leaving group can be readily recovered and reused for preparing the starting materials.

Efficient synthesis method of 2,3-indanone

The invention discloses an efficient synthesis method of 2,3-indanone. A heating reaction is carried out on o-substituted benzaldehyde and alkyne in an organic solvent under the catalysis of nickel and a phosphine ligand under the action of an alkali to obtain a 2,3-indanone product. O-substituted benzaldehyde and alkyne are used as raw materials, and the 2,3-indanone product is obtained in one step under the catalysis of metal nickel and the phosphine ligand under the action of the alkali, so the operation is simple and convenient, the regioselectivity is high, and the method is cheap and hasa good application prospect, and can be applied to efficient synthesis of natural products, medicines and materials.

Synthesis of Indenones via Palladium-Catalyzed Ligand-Free Carbonylation

A palladium-catalyzed ligand-free carbonylation reaction has been developed for the synthesis of indenones. Under CO atmosphere, this cascade reaction proceeded smoothly to provide the desired indenones in moderate to excellent yields with good functional-group compatibility. The mechanistic investigations suggested the in situ formation of palladium nanoparticles and this transformation was driven by a controlled reaction sequence of alkyne insertion followed by carbonylation and annulation to form the indenone framework. (Figure presented.).

Water-assisted metal-free catalyzed cyclization of 2-alkynylarylketones: A facile approach to indenones

A simple and directed synthetic strategy starting from 2-alkynylarylketones was developed for the construction of various indenones under metal-free and water-assisted conditions. This intramolecular cyclization reaction could well tolerate a wide range of functional groups, and the corresponding functionalized indenones were obtained in moderate to excellent yields (up to 94%). In addition, the possible mechanism of this reaction may involve isobenzofuranium intermediates.

Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of: O -methoxycarbonylphenylboronic acid with alkynes

Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones in good yields. Excellent regioselectivities were observed, when silyl aryl alkynes were used. The intermediate 3-silyl-2-aryl-substituted indenones were converted to 2,3-diaryl indenones by a three-step protocol involving C-Si bromination and Suzuki-Miyaura coupling reaction.

Cobalt(III)-catalyzed annulation of esters and alkynes: A facile route to indenones

An efficient protocol for the synthesis of indenones has been developed via the annulation of benzoic esters and internal alkynes by exploiting the cobalt catalyst.

Gold-Catalyzed Ammonium Acetate Assisted Cascade Cyclization of 2-Alkynylarylketones

An ammonium acetate assisted gold-catalyzed cascade cyclization reaction of 2-alkynylarylketones is described. Under the reported conditions, a gold-catalyzed intramolecular cyclization of 2-alkynylarylketones takes place through two competing reaction mechanisms?-?a 5-exo-dig or a 6-endo-dig cyclization-leading to two regioisomeric intermediates: isobenzofuranium or isobenzopyrylium. In the presence of ammonium acetate, the two intermediate compounds undergo further rearrangement to 2,3-disubstituted indenones and 1,3-disubstituted isoquinolines, respectively. While both reaction pathways proceed via a cyclization-rearrangement cascade, the gold-mediated 5-exo-dig process is especially notable, as it provides a novel cyclization protocol of 2-alkynylarylketones.