53786-92-8Relevant 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.
different nuclear ruthenium palladium double-ring metal compound and its preparation method and application
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Paragraph 0073; 0074, (2016/10/07)
The invention discloses a heteronuclear ruthenium palladium bicyclic metal compound and a preparation method and an application thereof and belongs to the technical field of organic synthesis. The metal compound is easily prepared and modified, stable in
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.
Gold-catalyzed formal cycloaddition of 2-ethynylbenzyl ethers with organic oxides and α-diazoesters
Pawar, Samir Kundlik,Wang, Chiou-Dong,Bhunia, Sabyasachi,Jadhav, Appaso Mahadev,Liu, Rai-Shung
, p. 7559 - 7563 (2013/07/26)
A world of possibilities: Gold-catalyzed reactions of 2-ethynylbenzyl ethers with organic oxides and α-diazoesters gave 1,3-dihydroisobenzofuran and naphthalene derivatives, respectively (see scheme; EWG=electron-withdrawing group). Mechanisms for the formation of the formal cycloadducts were elucidated by isotope labeling. Copyright
Synthesis of optically pure 1-amino-3-aryl indanes exemplified by (+)-indatraline
N?rager, Niels Gr?n,Lorentz-Petersen, Linda Luise Reeh,Lyngs?, Lars Ole,Kehler, Jan,Juhl, Karsten
supporting information; experimental part, p. 1753 - 1755 (2011/09/16)
A versatile procedure for the synthesis of optically pure 1-amino-3-aryl indanes is presented, exemplified by the synthesis of the triple uptake inhibitor (+)-indatraline (1). Georg Thieme Verlag Stuttgart · New York.
Versatile synthesis of 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones
Pueschl, Ask,Rudbeck, Hans Christian,Faldt, Andre,Confante, Allesia,Kehler, Jan
, p. 291 - 295 (2007/10/03)
We have developed a novel and versatile synthesis of racemic 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones. This method is especially attractive because it avoids strong acidic conditions and consequently a larger number of sensitive functional groups are accepted during synthesis compared with existing methods.
Cyclization of 1-phenyl-2-propen-1-ones into 1-indanones using H-zeolite and other solid acids. The role of mono- and dicationic intermediates
Koltunov, Konstantin Yu.,Walspurger, Stéphane,Sommer, Jean
, p. 8391 - 9394 (2007/10/03)
Cyclization of aryl vinyl ketones into 1-indanones was previously known to proceed only in drastic acidic or superacidic conditions due to the necessity of dicationic, superelectrophilic activation of starting compounds. In this paper, we disclose that available solid acids such as HUSY-zeolite, sulfated zirconia or heteropolyacid, H3PW12O40 can be successfully applied instead of superacids to perform these and related reactions. The cases, when the effective excess of acidic sites of the solid is required to carry out the reaction, are interpreted in terms of key dicationic (superelectrophilic) intermediates on the solid.
