3312-38-7

Upstream product

• 4767-61-7 3-(4-methoxybenzylidene)phthalide 
• 108-86-1 bromobenzene 
• 117-37-3 anisindione 
• 7380-78-1 4-(phenylethynyl)anisole 
• 26260-02-6 2-iodobenzaldehyde 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 104-94-9 4-methoxy-aniline 
• 1370697-68-9 (2-((4-methoxyphenyl)ethynyl)phenyl) (phenyl)methanone 
• 94796-78-8 3-bromo-2-(4-methoxyphenyl)-1H-inden-1-one 
• 98-80-6 phenylboronic acid 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 374538-03-1 2-methoxycarbonylphenylboronic acid 

Downstream Products

• 13304-40-0 2-(4-hydroxyphenyl)-3-phenyl-1-indenone 
• 52033-66-6 2-(4-methoxyphenyl)-3-phenyl-1H-indene 

Relevant academic research and scientific papers

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.

Gold Catalysis of Non-Conjugated Haloacetylenes

Gold-catalyzed reactions of conjugated haloacetylenes are well known and usually result in the formation of addition or dimerization products. Herein, we report a gold-catalyzed reaction of non-conjugated haloacetylenes, which leads exclusively to the hal

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.).

An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water

A one-pot synthesis of indenones is presented. The process involves palladium-catalyzed annulation of ortho-halobenzaldehydes with internal alkynes. Notably, it proceeded successfully in water as the sole, and green, solvent. Significantly, unlike in earlier reports, this protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes. Further, the strategy was extended to a one-pot synthesis of a neolignan natural product.

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.

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.

Cobalt-catalyzed arylation of aldimines via directed C-H bond functionalization: Addition of 2-arylpyridines and self-coupling of aromatic aldimines

A cobalt-N-heterocyclic carbene catalyst, in combination with an appropriate Grignard reagent, promotes a chelation-assisted aromatic C-H functionalization reaction via addition to an aromatic aldimine. The Royal Society of Chemistry 2012.

Stereoselective palladium-catalyzed α-arylation of 3-aryl-1-indanones: An asymmetric synthesis of (+)-pauciflorol F

Highly stereoselective, palladium-catalyzed α-arylation reactions of 3-aryl-1-indanones with aryl bromides are described. The use of sodium tert-butoxide as a base in this process is required to elevate the efficiencies and stereoselectivities of these re

A facile approach to the construction of 1H-inden-1-one

The one-pot synthesis of 1H-inden-1-one from 1-(2-bromoaryl)prop-2-en-1-ol was described. The reaction involved a sequential intramolecular Heck reaction followed by an aerial oxidation of allylic alcohol. Georg Thieme Verlag Stuttgart.

Synthesis of Indenones via Palladium-Catalyzed Annulation of Internal Alkynes

A number of 2,3-disubstituted 1-indenones have been prepared in fair to good yields by treating o-iodo- or o-bromobenzaldehyde with various internal alkynes in the presence of a palladium catalyst.Synthetically, the methodology provides an especially conv