17371-60-7Relevant academic research and scientific papers
Synthesis of carbazoles by a balanced four component condensation
Cochard, Fabien,Laronze, Marie,Sigaut, Philippe,Sapi, Janos,Laronze, Jean-Yves
, p. 1703 - 1707 (2004)
An access to functionalised tetrahydrocarbazoles by a multicomponent reaction including 2-substituted indoles, aromatic aldehydes and Meldrum's acid is described.
Reactivity of the chiral metallic Bronsted acid [(η6- p -MeC6H4 i Pr)Ru(κ3 P, O,O'- POH)][SbF6]2 (POH = (S C1, R C2)-Ph2PC(Ph)HC(OH)HCH2OMe) toward aldimines
Pardo, Pilar,Carmona, Daniel,Lamata, Pilar,Rodrguez, Ricardo,Lahoz, Fernando J.,Garca-Ordua, Pilar,Oro, Luis A.
, p. 6927 - 6936 (2014)
Dichloromethane solutions of complex 1 catalyze both the aza-Diels-Alder (ADA) reaction of aldimines with cyclopentadiene and the aza-Friedel-Crafts (AFC) reaction between aldimines and indoles. Racemic adducts were obtained in both cases. NMR measurements of mixtures of the aldimine N-(4-methylbenzylidene)aniline (I) and 1, in a 20/1 molar ratio, reveal the formation of the deprotonated compound 2 and the corresponding iminium cation HI+ (H-N+). This cation is responsible for the achiral catalysis. Below 273 K, in 1/1 molar ratio mixtures of 1 and I, the chiral species 1·I (O-H···N) and 2·HI+ (O-···H-N+) were formed by intermolecular hydrogen bonding and proton transfer, respectively. The latter solutions catalyze stoichiometrically the ADA reaction between aldimine I and HCp with 16% ee. With 5 mol % of catalyst loading, a 6% ee can be obtained if the aldimine is slowly added to the solution (20 equiv in 60 h). Above 273 K, solutions containing 1 and aldimine I irreversibly evolve to the aniline complex 3, which was isolated as a racemic mixture. The molecular structure of 3 has been determined by X-ray diffractometric methods. Hydride 5, an intermediate in this reaction, has been isolated and spectroscopically characterized. On the basis of synthetic and spectroscopic studies, a plausible pathway for the formation of 3 from 1 is proposed.
Anodically Triggered Aldehyde Cation Autocatalysis for Alkylation of Heteroarenes
Liu, Caiyan,Xiao, Zihui,Wu, Shuhua,Shen, Yongli,Yuan, Kedong,Ding, Yi
, p. 1997 - 2001 (2020/02/27)
Alkylation of heteroarenes by using aldehydes is a direct approach to increase molecular complexity, which however often involves the use of stochiometric oxidant, strong acid, and high temperature. This study concerns an energy-efficient electrochemical alkylation of heteroarenes by using aldehydes under mild conditions without mediators. Interestingly, the graphite anode can trigger aldehyde cationic species, which act as the effective autocatalysts to react with a range of heteroarenes to produce the corresponding products with excellent regioselectivity and in high yields. Compared to the traditional electro-synthesis approaches, this electro-triggered reaction provides an electricity-saving and eco-friendly route to high-value chemicals.
Palladium-catalyzed carbonylative bis(indolyl)methanes synthesis with TFBen as the CO source
Qi, Xinxin,Ai, Han-Jun,Zhang, Ning,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
, p. 74 - 77 (2018/04/20)
An efficient and convenient palladium-catalyzed carbonylative procedure for the synthesis of bis(indolyl)methanes has been established for the first time. With TFBen (benzene-1,3,5-triyl triformate) as the solid CO source, aryl iodides and indoles were tr
