17932-18-2Relevant 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.
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.).
An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
Ramesh, Karu,Satyanarayana, Gedu
, p. 4135 - 4146 (2018/08/11)
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.
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.
Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of: O -methoxycarbonylphenylboronic acid with alkynes
Ueda, Mitsuhiro,Ueno, Tamami,Suyama, Yuki,Ryu, Ilhyong
supporting information, p. 13237 - 13240 (2016/11/17)
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.
MeOTf-induced carboannulation of arylnitriles and aromatic alkynes: A new metal-free strategy to construct indenones
Yan, Xiaoyu,Zou, Song,Zhao, Peng,Xi, Chanjuan
supporting information, p. 2775 - 2777 (2014/03/21)
MeOTf-induced carboannulation of arylnitriles and aromatic alkynes for synthesis of indenones under metal-free conditions has been described. When ortho-substituted benzonitriles were used, indeno[1,2-c]isoquinolines were formed.
Regioselective construction of indene skeletons by palladium-catalyzed annulation of alkynylborates with o-iodophenyl ketones
Shimamoto, Yasuhiro,Sunaba, Hanako,Ishida, Naoki,Murakami, Masahiro
, p. 1421 - 1424 (2013/04/23)
A palladium-catalyzed annulation reaction of alkynylborates with o-iodophenyl ketones to form indenes is described. Highly substituted indene skeletons are efficiently constructed with site-specific installation of the substituents. Alkynylborates react w
A facile approach to the construction of 1H-inden-1-one
Chen, Bo,Xie, Xingang,Lu, Jiangping,Wang, Qiaoling,Zhang, Jiyong,Tang, Shouchu,She, Xuegong,Pan, Xinfu
, p. 259 - 262 (2007/10/03)
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
Larock, R. C.,Doty, M. J.,Cacchi, S.
, p. 4579 - 4583 (2007/10/02)
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
