4212-33-3Relevant articles and documents
Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature
Venkatesh, Rapelly,Singh, Adesh Kumar,Lee, Yong Rok,Kandasamy, Jeyakumar
, p. 7832 - 7837 (2021/09/28)
Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.
Synthesis of 2-substituted indole with Hantzsch ester catalyzed by palladium
Li, Yanan,Wang, Bo,Xing, Ruiguang
, p. 295 - 303 (2019/08/01)
An efficient reductive cyclization of o-nitrobenzyl ketone compounds was achieved by using a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. 2-Substituted indoles were obtained in good yields. Investigation of the mechanism suggests that palladium hydride promotes the reduction of nitro group, and acetic acid was beneficial for the loss of water to produce the intended product. This reaction system can not only broaden the use of Hantzsch 1,4-dihydropyridine ester, but it also provides a novel approach for preparing indole compounds.
Synthesis of new 3-substituted 1-hydroxy-2-phenylindoles using sulfur-containing nucleophiles
Kim, Hyejin,Lee, Sang Hyup
, p. 2004 - 2017 (2016/11/25)
The synthesis of new 3-[(acyl(or alkyl)thio)methyl]-1-hydroxy-2-phenylindoles 1 are presented. The substrates 2 obtained by each efficient three-step synthesis were treated, in the presence of SnCl2·2H2O, with nucleophiles such as th
Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation
Zhang, Song-Lin,Yu, Ze-Long
supporting information, p. 10511 - 10515 (2016/11/18)
Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones is described in this report by using a general Pd-catalyzed tandem reaction of β-hydroxy carbonyl compounds with aryl halides bearing an ortho-nitro, -ester or -cyano substituent. A key retro-aldol/α-arylation reaction is involved that merges classic Pd cross-coupling chemistry with novel Pd-promoted retro-aldol C-C activation to produce α-arylated ketones or esters. Subsequent intramolecular condensation of the carbonyl with the ortho-synthon gives target heterocycles. The use of common, commercially available and cheap substrates and catalyst system adds additional synthetic advantages to the conceptual significance.
Ruthenium-catalyzed cascade C-H functionalization of phenylacetophenones
Mehta, Vaibhav P.,Garcia-Lopez, Jose-Antonio,Greaney, Michael F.
supporting information, p. 1529 - 1533 (2014/03/21)
Three orthogonal cascade C-H functionalization processes are described, based on ruthenium-catalyzed C-H alkenylation. 1-Indanones, indeno indenes, and indeno furanones were accessed through cascade pathways by using arylacetophenones as substrates under conditions of catalytic [{Ru(p-cymene)Cl2}2] and stoichiometric Cu(OAc) 2. Each transformation uses C-H functionalization methods to form C-C bonds sequentially, with the indeno furanone synthesis featuring a C-O bond formation as the terminating step. This work demonstrates the power of ruthenium-catalyzed alkenylation as a platform reaction to develop more complex transformations, with multiple C-H functionalization steps taking place in a single operation to access novel carbocyclic structures. Carbon coupling cascade: Arylacetophenones react with Michael acceptors under ruthenium catalysis to set up triple and quadruple C-H functionalization pathways. Through choice of reaction conditions, novel indanone carbacycles, indeno indene carbacycles, and indeno furanone heterocycles can each be accessed in a single step.
Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones
Coffman, Keith C.,Palazzo, Teresa A.,Hartley, Timothy P.,Fettinger, James C.,Tantillo, Dean J.,Kurth, Mark J.
supporting information, p. 2062 - 2065 (2013/06/05)
Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-,
Palladium and copper catalyzed one-pot Sonogashira reaction of 2-nitroiodobenzenes with aryl acetylenes and subsequent regioselective hydration in water: Synthesis of 2-(2-nitrophenyl)-1-aryl ethanones
Ahammed, Sabir,Dey, Raju,Ranu, Brindaban C.
, p. 3697 - 3701 (2013/07/05)
An attempted Sonogashira reaction of 2-nitroiodobenzene and phenyl acetylene catalyzed by Pd(PPh3)4/Cu in water in the presence of pyrrolidine proceeds with simultaneous regioselective hydration of the Sonogashira alkyne leading to the corresponding aryl ketone. A series of functionalized 2-(2-nitrophenyl)-1-aryl ethanones are obtained in high yields by this procedure.
Visible-light-mediated α-arylation of enol acetates using aryl diazonium salts
Hering, Thea,Hari, Durga Prasad,Koenig, Burkhard
, p. 10347 - 10352 (2013/01/15)
Visible light mediates efficiently the α-arylation of enol acetates by aryl diazonium salts under mild conditions using [Ru(bpy)3]Cl 2 as a photoredox catalyst. The broad scope of the reaction toward various diazonium salts and enol acetates was explored. The application of this reaction in the concise synthesis of 2-substituted indoles was demonstrated
Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles
Jadhav, Jagannath,Gaikwad, Vipul,Kurane, Rajanikant,Salunkhe, Rajashri,Rashinkar, Gajanan
, p. 2511 - 2515,5 (2012/12/11)
An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles.
Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles
Jadhav, Jagannath,Gaikwad, Vipul,Kurane, Rajanikant,Salunkhe, Rajashri,Rashinkar, Gajanan
, p. 2511 - 2515 (2013/01/13)
An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles. Georg Thieme Verlag Stuttgart · New York.
