1210-39-5Relevant articles and documents
PALLADIUM-CATALYZED ACYL-O BOND FISSION-PHENYLATION REACTION OF ALLYL ESTERS WITH BENZENE
Fujiwara, Yuzo,Yoshidomi, Michiaki,Kuromaru, Hiroaki,Taniguchi, Hiroschi
, p. C36 - C38 (1982)
The palladium-catalyzed acyl-O bond fission-phenylation reaction of allyl esters with benzene has been found to give cinnamaldehyde derivatives in one step in modest yields.
Optimization of the Mizoroki-Heck reaction using Design of Experiment (DoE)
Aggarwal, Varinder K.,Staubitz, Anne C.,Owen, Martin
, p. 64 - 69 (2006)
The influence of the variables concentration, temperature, time, and amounts of base and palladium on the yield of a Heck reaction was investigated using statistical methods (DoE) in a systematic sequential study. This revealed that temperature, concentration, and amount of palladium were the most important variables with a factor interaction between temperature and concentration. Through this approach, the yield of the Heck reaction was improved from 57% to 98% (89% isolated) with concomitant reduction of palladium loading from 3% to 0.5%.
Heck transformations of biological compounds catalyzed by phosphine-free palladium
Tarnowicz-Ligus, Stanis?awa,Trzeciak, Anna M.
, (2018)
The development and optimization of synthetic methods leading to functionalized biologically active compounds is described. Two alternative pathways based on Heck-type reactions, employing iodobenzene or phenylboronic acid, were elaborated for the arylation of eugenol and estragole. Cinnamyl alcohol was efficiently transformed to saturated arylated aldehydes in reaction with iodobenzene using the tandem arylation/isomerization sequential process. The arylation of cinnamyl alcohol with phenylboronic acid mainly gave unsaturated alcohol, while the yield of saturated aldehyde was much lower. Catalytic reactions were carried out using simple, phosphine-free palladium precursors and water as a cosolvent, following green chemistry rules as much as possible.
Oxime ligands for Pd catalysis of the Mizoroki–Heck reaction, Suzuki–Miyaura coupling & annulation reactions
Bangar, Pronnoy G.,Nahide, Pradip D.,Meroliya, Heena K.,Waghmode, Shobha A.,Iyer, Suresh
, p. 308 - 316 (2021)
Monodentate and bidentate chelating oximes are readily available ligands for the Pd catalysis of the Mizoroki–Heck reaction and the Suzuki coupling. High yields were obtained in the Suzuki coupling in aqueous dioxane with TBABr as additive. The oximes can be easily synthesized from the corresponding ketones or aldehydes and thus provide a very large number of nitrogen-based ligands. They have the advantage of not undergoing oxidative degradation, common for phosphine ligands. Chelating oximes with Pd(OAc)2, activate aryl iodides to give high yields of the substitution products in the Mizoroki–Heck reactions as well as the Suzuki coupling. Acetophenone oxime ligand with Pd(OAc)2, catalyzed the reaction of aryl iodides with 1,2-disubstituted alkenes in moderate to high yields. As a test example, the LaRock indole annulation and synthesis of isocoumarin were achieved with acetophenone oxime ligand and Pd(OAc)2 in high yields.
Pd-catalysed arylation of propan-1-ol and derivatives: Oxidative role of the arylating agent
Bagnell,Kreher,Strauss
, p. 29 - 30 (2001)
With excess PhI under Pd catalysis, 1-PrOH was converted to a mixture of 3,3-diphenylpropenal and trans-2,3-diphenylpropenal by a concerted, oxidative sequence that involved two arylative couplings and an olefinic aldehyde that was generated in situ.
Selenated NHC-Pd(II) catalyzed Suzuki-Miyaura coupling of ferrocene substituted β-chloro-cinnamaldehydes, acrylonitriles and malononitriles for the synthesis of novel ferrocene derivatives and their solvatochromic studies
Tomar, Vijesh,Upadhyay, Yachana,Srivastava, Avinash K.,Nemiwal, Meena,Joshi, Raj K.,Mathur, Pradeep
supporting information, (2021/04/05)
Suzuki-Miyaura coupling reaction between ferrocenyl/phenyl derivatives of (2-formyl-1-chlorovinyl)ferrocene, 3-chloro-3-ferrocenylacrylonitrile and (3-chloro-3-ferrocenylallylidene)malononitrile and arylboronic acid in the catalytic presence of a selenated NHC-Pd(II) full pincer complex was accomplished. Significantly, the couplings take place in water under normal atmospheric conditions, in contrast to many earlier reported Pd-catalysed reactions requiring inert atmosphere conditions. Solvatochromic studies of new ferrocene compounds revealed some interesting changes. Aggregation studies showed an increase of the absorbance with decrease of water content in the water/DMSO solvent mixture.
Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity
Bangar, Pronnoy G.,Jawalkar, Priyanka R.,Dumbre, Swapnil R.,Raut, Pallavi K.,Patil, Dharmaraj J.,Tv, Neethu,Sudhakaran, Shana,Iyer, Suresh
supporting information, p. 3796 - 3803 (2020/09/01)
Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu3P.HBF4 gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the reaction of aryl iodides with various 1,2-disubstituetd aryl alkenes.
Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3-Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses
Stephan, Marvin,Panther, Jesco,Wilbert, Fabio,Ozog, Pauline,Müller, Thomas J. J.
supporting information, p. 2086 - 2092 (2020/03/23)
3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller's CataCXium Ptb ligand under Jeffery's and Fu's conditions. The formation of these three-carbon building blocks is embedded into consecutive three- and pseudo-four-component syntheses of 3-(hetero)aryl and 3,5-diarylpyrazoles with a broad substitution pattern in moderate to excellent yield.
Deep eutectic solvent-catalyzed Meyer-Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions
Ríos-Lombardía, Nicolás,Cicco, Luciana,Yamamoto, Kota,Hernández-Fernández, José A.,Morís, Francisco,Capriati, Vito,García-álvarez, Joaquín,González-Sabín, Javier
supporting information, p. 15165 - 15168 (2020/12/21)
The Meyer-Schuster rearrangement of propargylic alcohols into α,β-unsaturated carbonyl compounds has been revisited by setting up an atom-economic process catalyzed by a deep eutectic solvent FeCl3·6H2O/glycerol. Isomerizations take place smoothly, at room temperature, under air and with short reaction times. The unique solubilizing properties of the eutectic mixture enabled the use of a substrate concentration up to 1.0 M with the medium being recycled up to ten runs without any loss of catalytic activity. This journal is
Palladium-Catalyzed Synthesis of β,β-Diaryl α,β-Unsaturated Ketones
Zheng, Yi-Lin,Xiao, Li,Xie, Qiong,Shao, Li-Ming
, p. 1455 - 1465 (2019/03/07)
We herein describe a versatile palladium-catalyzed synthesis of β,β-diaryl α,β-unsaturated ketones. A broad range of aryl halides react with β-arylbutanones to afford biologically useful, symmetrical and unsymmetrical ketones. The use of 4,5-diazafluoren-9-one and oxygen makes this one-pot reaction more applicable. A plausible mechanism involving palladium-catalyzed oxidative Heck-type cross-coupling is also proposed.
