3312-36-5Relevant academic research and scientific papers
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.
Iodine-Mediated Cyclization of ortho-Alkynylaryl Ketones for the Synthesis of Indenone Derivatives
Chuangsoongnern, Pennapa,Surinrach, Chareef,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
, p. 5102 - 5109 (2017/09/23)
A new method for the synthesis of indenone derivatives based on the I2-promoted cyclization of ortho-alkynylaryl ketones has been developed. This method provides a metal-free and convenient route for the regioselective synthesis of indenones using ortho-alkynylaryl ketones with predefined substituents to give indenone products in moderate to good yields.
Rhodium-Catalyzed Oxidative Decarboxylation Annulation Reactions of Mandelic Acids and Alkynes: An Efficient Synthetic Method for Indenones
Yu, Xiaobo,Duan, Yulian,Guo, Weijie,Wang, Tao,Xie, Qingxiao,Wu, Shutao,Jiang, Chenggong,Fan, Zixiong,Wang, Jianhui,Liu, Guiyan
, p. 1027 - 1034 (2017/04/21)
Efficient rhodium-catalyzed oxidative decarboxylation annulation reactions between mandelic acids and alkyne derivatives are described. The desired indenone products were obtained in medium to good yields under the optimized reaction conditions, which were a [RhCp*Cl2]2 catalyst (10.0 mol %) in combination with a PCy3 ligand (10.0 mol %) and AgSbF6 (10 mol %) and Cu(OAc)2 (20 mol %) additives. Many functional groups are compatible with the reaction under the optimized reaction conditions. This strategy provides a promising method for the construction of indenones from cheap and commercially available starting materials.
Palladium-catalyzed annulation of alkynes with ortho -halide-containing benzyl alcohols in aqueous medium
Feng, Jie,Lu, Guoping,Lv, Meifang,Cai, Chun
, p. 10561 - 10567 (2015/02/19)
The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate scopes. Moreover, the indenones obtained in this procedure can be further functionalized to form some more synthetic useful derivatives via an environmental-friendly way.
