1801-42-9Relevant articles and documents
MeOTf-Induced Carboannulation of Isothiocyanates and Aryl Alkynes with C=S Bond Cleavage: Access to Indenones
Zhao, Peng,Liu, Yu,Xi, Chanjuan
, p. 4388 - 4391 (2015)
MeOTf-induced carboannulation of alkyl isothiocyanates and aryl alkynes for the synthesis of indenones in good yields under metal-free conditions with C=S bond cleavage is described. The thioalkoxy group at the 3-position of the indenone can also be converted into other functional groups, such as phenyl, methylsulfonyl, amino, and ethoxy groups.
The effects of phosphine ligands on the benzannulation reaction of molybdenum carbene complexes with alkynes
Hsung,Hsung, Richard P.,Xu,Yao-Chang, Xu,Wulff,Wulff, William D.
, p. 8159 - 8162 (1995)
The effects of phosphine substitution at the metal on the reactions of group 6 pentacarbonyl Fischer carbene complexes with alkynes have been found not to be those expected from what is known about these reactions. The product distribution for the reaction of the molybdenum complex 5 with 3-hexyne changes dramatically from predominately indene product to predominately quinone product upon substitution of one of the CO ligands in 5a with a tri-n-butylphosphine.
Rhodium(I)-Catalyzed Carbonylative Annulation of Iodobenzenes with Strained Olefins and 4-Octyne in the Presence of Furfural Involving ortho-C–H Bond Cleavage
Furusawa, Takuma,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Morimoto, Tsumoru,Kakiuchi, Kiyomi
, p. 240 - 245 (2017)
The rhodium(I)-catalyzed carbonylative annulation of iodobenzenes with strained olefins in the presence of furfural as a carbonyl source, accompanied by ortho-C–H bond cleavage, is reported. The use of 4-octyne in place of strained olefins also leads to the formation of the corresponding inden-9-one. The timely release of the carbonyl moiety via the rhodium-catalyzed decarbonylation of furfural plays a decisive role in this reaction. (Figure presented.).
Rapid Formation of Fluoren-9-ones via Palladium-Catalyzed External Carbon Monoxide-Free Carbonylation
Konishi, Hideyuki,Futamata, Suguru,Wang, Xi,Manabe, Kei
, p. 1805 - 1809 (2018)
A Pd-catalyzed carbonylation reaction for the synthesis of fluoren-9-ones from 2-halogenated biphenyls using phenyl formate as a carbon monoxide surrogate was achieved. The combined use of cesium carbonate and o-anisic acid resulted in a remarkable rate e
Alkylations of Tetracarbonyl(phosphine)chromium and Pentacarbonylchromium Carbene Complexes and Their Reactions with Selected Acetylenes
Xu, Yao-Chang,Wulff, William D.
, p. 3263 - 3275 (1987)
The thermodynamic acidity of (methylmethoxymethylene)tetracarbonyl(tri-n-butylphosphine)chromium (1b) was found to be 6 orders of magnitude less than that of (methylmethoxymethylene)pentacarbonylchromium (1a).The anion 2b is generated from 1b by deprotona
Synthesis of Indenones Via Palladium-Catalyzed Carbonylation with Mo(CO)6 as a CO Surrogate
Li, Dong-Kun,Zhang, Bo,Ye, Qi,Deng, Wei,Xu, Zheng-Yang
supporting information, p. 441 - 449 (2022/02/23)
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
Ochiai, Shiho,Sakai, Asumi,Usuki, Yoshinosuke,Kang, Bubwoong,Shinada, Tetsuro,Satoh, Tetsuya
supporting information, (2021/04/23)
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.
Mechanochemical Solvent-Free Synthesis of Indenones from Aromatic Carboxylic Acids and Alkynes
Li, Liang,Wang, Guan-Wu
, p. 14102 - 14112 (2021/09/07)
The mechanochemical solvent-free synthesis of indenones from aromatic carboxylic acids and alkynes was achieved through triflic anhydride (Tf2O)-induced cyclization reaction. A variety of indenones including a bioactive PPARγagonist were obtained in up to 90% yield at room temperature. The present protocol has the advantages of mild reaction conditions, high reaction efficiency, and feasibility of scalable synthesis, providing a facile and sustainable route to diverse indenones.
Divergent Synthesis of α-Aroyloxy Ketones and Indenones: A Controlled Domino Radical Reaction for Di- A nd Trifunctionalization of Alkynes
Jafarpour, Farnaz,Azizzade, Meysam,Golpazir-Sorkheh, Yekta,Navid, Hamed,Rajai-Daryasarei, Saideh
, p. 8287 - 8294 (2020/07/15)
Three different modes of aldehyde/alkyne assembly through a controlled radical reaction are devised. While a double C-H activation/annulation leads to indenones, a concurrent oxidation of both aldehydes and alkynes in the course of their connection offers
Preparation method of polysubstituted indanone derivative
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Paragraph 0030-0086, (2020/11/01)
The invention relates to a polysubstituted indanone derivative and a preparation method thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the followingsteps: in a solvent, reacting aryl aldehyde with an alkyne derivative under an illumination condition, and carrying out post-treatment to generate the polysubstituted indanone derivative. The methodhas the advantages of simple operation, environmental friendliness, high regioselectivity, low cost, mild reaction conditions, simple operation, wide substrate range, simple post-treatment, high yield, high purity and the like.
