53786-91-7Relevant academic research and scientific papers
Palladium Nanoparticles-Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction
Parveen, Naziya,Sekar, Govindasamy
, p. 4581 - 4595 (2019/09/03)
An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2′-iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2′-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. (Figure presented.).
Synthesis of 3-aryl-1-indanones via CsF-promoted coupling of arylboronic acids with N-tosylhydrazones
Liu, Yueqiang,Chen, Lingjuan,Liu, Yan,Liu, Ping,Dai, Bin
, p. 40 - 43 (2018/02/28)
A series of 17 3-aryl-1-indanones, four of which are novel, were prepared in good yield via a CsF-promoted reductive cross-coupling of the monotosylhydrazone of a 1,3-indanedione with an arylboronic acid. The method demonstrates wide substrate scope and good functional group tolerance. Moreover, the 3-aryl-1-indanones could also be prepared on a multi-gram scale.
Gold(I)-Catalyzed Addition of Silylacetylenes to Acylsilanes: Synthesis of Indanones by C-H Functionalization through a Gold(I) Carbenoid
González, Jairo,Santamaría, Javier,Ballesteros, Alfredo
supporting information, p. 13678 - 13681 (2015/11/16)
A gold(I)-catalyzed synthesis of indanones from trimethylsilylacetylenes and acylsilanes is presented. The reaction is initiated through a synergistic acylsilane activation-gold acetylide formation and involves consecutive alkyne σ-gold(I) addition, π-activation, and 1,2-migration of a silyl group. Studies performed on the reaction mechanism allowed to establish the nature of the silyl migrating group and invoke the participation of a gold(I) carbenoid intermediate. The reaction is completed by a gold(I) C-H functionalization step.
Electronic effects of substituents on the stability of the iridanaphthalene compound [IrCp{C(OMe)CHC(o-C6H4)(Ph)}(PMe3)]PF6
Talavera,Bravo,Castro,Garca-Fontn,Hermida-Ramn,Bolao
, p. 17366 - 17374 (2015/01/09)
Iridanaphthalene complexes are synthesized from the corresponding methoxy(alkenyl)carbeneiridium compounds. The electronic character of the substituents on the 6-position of the metallanaphthalene ring is crucial from the point of view of the stability of the iridanaphthalene, [IrCp{C(OMe)CHC(o-C6H4)(Ph)}(PMe3)]PF6, vs. its transformation to the corresponding indanone derivatives. Stability studies of the iridanaphthalene compounds revealed that strong electron donor substituents (-OMe) stabilize the iridanaphthalene, while weak electron donor (-Me) and electron withdrawing (-NO2) groups favor the formation of indanone derivatives. Two possible indanone isomers can be obtained in the conversion of the unstable iridanaphthalene complexes and a mechanism for the formation of these isomers is proposed. This journal is
Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 2-indanones chemoselectively: Effects of ligands and solvents
Wang, Chiou-Dong,Hsieh, Yi-Feng,Liu, Rai-Shung
supporting information, p. 144 - 152 (2014/03/21)
The selective syntheses of 1- and 2-indan-one compounds from 2-ethynylbenzyl ethers have been achieved with suitable catalysts and solvents. The highly acidic [tris(pentafluorophenyl)phos-phine]gold hexafluoroantimonate [(C6F5)3AuSbF6] in nitromethane (MeNO2) preferably gives 1-indan-ones whereas [(ortho-biphenyl) di(tert-butyl)phosphine] gold triflimide [(tBu)2(o-biphenyl) AuNTf2] in dichloroethane tends to form 2-indanone derivatives. For 2-indanone products, we isolated two indenyl methyl ethers for deuterium labeling analyses, providing evidence for p-alkyne activation.
Superacid-promoted dual C-C bond formation by Friedel-Crafts alkylation and acylation of ethyl cinnamates: Synthesis of indanones
Venkat Ramulu, Bokka,Gopi Krishna Reddy, Alavala,Satyanarayana, Gedu
, p. 868 - 872 (2013/05/22)
A superacid (triflic acid) promoted dual C-C bond formation via intermolecular Friedel-Crafts alkylation (Michael addition type) and intramolecular acylation for the efficient synthesis of 3-substituted indan-1-ones is presented. This method was successful in activating ethyl cinnamates towards dual aromatic electrophilic substitution. Moreover, it enabled us to synthesize novel spirotetracyclic systems. Georg Thieme Verlag Stuttgart · New York.
