1264166-21-3Relevant academic research and scientific papers
Synthesis of Indenones Via Palladium-Catalyzed Carbonylation with Mo(CO)6 as a CO Surrogate
Deng, Wei,Li, Dong-Kun,Xu, Zheng-Yang,Ye, Qi,Zhang, Bo
, (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.
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.
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.
Preparation method of polysubstituted indanone derivative
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Paragraph 0123-0125, (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.
Synthesis of Indenones via Palladium-Catalyzed Ligand-Free Carbonylation
Song, Juan,Sun, Haisen,Sun, Wei,Fan, Yuxuan,Li, Cui,Wang, Haotian,Xiao, Kang,Qian, Yan
supporting information, p. 5521 - 5527 (2019/11/14)
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.).
A polysubstituted indenone derivatives and its preparation method (by machine translation)
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Paragraph 0088-0091, (2019/04/17)
The present invention discloses a multi-substituted indenone derivatives and its preparation method, its structural formula is: Wherein R1 Is alkyl, halogen, methoxy, trifluoromethyl, N, N - dimethyl or methylthio, R2 is aryl. Synthesis of this invention has a plurality of substituted base yinyin alkone derivatives, from the point of view of pharmaceutical chemistry has far-reaching significance. The method of this invention easily obtained raw material, economic low-cost, high yield, mild reaction conditions, wide substrate range, easy post treatment. (by machine translation)
Palladium(ii)-catalyzed synthesis of indenones through the cyclization of benzenecarbaldehydes with internal alkynes
Kashanna, Jajula,Aravind Kumar, Rathod,Kishore, Ravada
, p. 31162 - 31168 (2019/10/28)
The palladium(ii)-catalyzed carbocyclization of benzenecarbaldehydes with internal alkynes to afford 2,3-disubstituted indenones was reported. The annulation reaction proceeded through the transmetalation of Pd(ii) with an aromatic aldehyde and the insertion of internal alkynes, followed by cyclization via the intramolecular nucleophilic addition of intermediate organopalladium(ii) species to the aldehyde group. This reaction proceeded in moderate to good yields with high regioselectivity.
Ferrocene-Initiated Oxidative Cyclization of Benzaldehyde with Alkyne: New Strategy to Substituted Indenones
Feng, Yadong,Zhang, Hong,Yu, Yunliang,Yang, Lei,Cui, Xiuling
supporting information, p. 2740 - 2744 (2019/04/17)
A ferrocene-initiated oxidative cyclization of benzaldehyde with alkyne was successfully developed as a novel strategy for direct access to substituted indenones in high yields. The commercially available and cheap ferrocene was employed as an initiator. This transformation could proceed smoothly with a low initiator loading (0.5 mol-%) and provide the titled products up to 90 % yield with atom-, step-economy and good substrates tolerance. The indenones obtained would be important building blocks in organic synthesis.
Rhodium-catalyzed carbonylative annulation of 2-bromobenzylic alcohols with internal alkynes using furfural via β-aryl elimination
Furusawa, Takuma,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Morimoto, Tsumoru,Kakiuchi, Kiyomi
supporting information, p. 926 - 929 (2017/06/27)
In spite of the significant progress made in transformations of unstrained benzylic (tert-)alcohols through β-aryl elimination, catalytic carbonylation has not yet been developed extensively because alkoxycarbonylation is probably favored over β-aryl elim
Cobalt(III)-catalyzed annulation of esters and alkynes: A facile route to indenones
Yu, Wenlong,Zhang, Wei,Liu, Zhanxiang,Zhang, Yuhong
supporting information, p. 6837 - 6840 (2016/06/01)
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.
