10408-73-8Relevant articles and documents
Rhodium-catalyzed annulation reactions of 2-cyanophenylboronic acid with alkynes and strained alkenes
Miura, Tomoya,Murakami, Masahiro
, p. 3339 - 3341 (2005)
(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.
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.
Efficient synthesis method of 2,3-indanone
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Paragraph 0056-0060, (2020/07/03)
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.
Water-assisted metal-free catalyzed cyclization of 2-alkynylarylketones: A facile approach to indenones
Zhang, Shuai,Bai, Xue-Ting,Chen, Dan-Yun,Chen, Pei,Zhang, Qian-Qian,Wang, Yan-Bo
, p. 31142 - 31147 (2017/07/11)
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.
