199393-24-3Relevant articles and documents
Pd-catalyzed oxidative olefination of arenes with olefins via C-H activation: Retention of the leaving group
Mao, Jincheng,Yang, Xiaojiang,Wang, Dingli,Zhang, Yang
, p. 2050 - 2055 (2016/03/19)
Pd-catalyzed direct oxidative olefination of arenes with olefins via C-H activation is described in the absence of any chelating directing groups. For Pd-catalyzed oxidative coupling between arenes and allyl acetate, it was observed the retention of the leaving group.
Versatile palladium-catalyzed C-H olefination of (hetero)arenes at room temperature
She, Zhijie,Shi, Yang,Huang, Yumin,Cheng, Yangyang,Song, Feijie,You, Jingsong
supporting information, p. 13914 - 13916 (2015/01/09)
The room-temperature oxidative C-H/C-H cross-couplings between (hetero)arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)2], generated in situ from Pd(OAc)2and TFA, as the catalyst and cheap (NH4)2S2O8as the oxidant under air.
Wittig reactions in water media employing stabilized ylides with aldehydes. Synthesis of α,β-unsaturated esters from mixing aldehydes, α-bromoesters, and Ph3P in aqueous NaHCO3
El-Batta, Amer,Jiang, Changchun,Zhao, Wen,Anness, Robert,Cooksy, Andrew L.,Bergdahl, Mikael
, p. 5244 - 5259 (2008/02/07)
(Chemical Equation Presented) Water is demonstrated to be an effective medium for the Wittig reaction over a wide range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities (up to 99%) are achieved, and the rate of the reactions in water is unexpectedly accelerated. The efficiency of water as a medium in the Wittig reaction is compared to conventional organic solvents ranging from carbon tetrachloride to methanol. The aqueous Wittig reaction works best when large hydrophobic entities are present, such as aromatic, heterocyclic aromatic carboxaldehydes, and long-chain aliphatic aldehydes with triphenylphosphoranes. The E/Z-isomeric ratio of the Wittig products appears dependent on the electron-accepting/donating capacity and the location of the substituents present in the aromatic ring. The effect of additives, such as benzoic acid, LiCl, and sodium dodecyl sulfate (SDS), on the Wittig reaction has been explored. The Wittig reaction can also be conducted in the presence of acidic entities, such as phenols and carboxylic acids. In addition, large α-substituents in the aliphatic aldehydes do not jeopardize the reaction. It is also demonstrated that hydrates of aldehydes can be used directly in the aqueous Wittig reaction as substrates. The scope of the aqueous Wittig reaction is extended to 24 examples of one-pot mixtures of Ph3P, α-bromoesters, and aldehydes in sodium bicarbonate solution (at 20°C for 40 min to 3 h) to provide Wittig products of up to 99% yield and up to 98% E-selectivity. Since water is inexpensive, extremely easy to handle, and represents no environmental concerns, it should be considered a possible medium for new organic reactions.
Oxidative Coupling of 1-(2,6-Dichlorobenzoyl)pyrroles and -pyrazoles and Alkyl Acrylates by Palladium(II) Acetate
Itahara, Toshio,Kawasaki, Kazukuni,Ouseto, Fumio
, p. 3488 - 3493 (2007/10/02)
Treatments of 1-(2,6-dichlorobenzoyl)-, 3-acetyl-1-(2,6-dichlorobenzoyl)-, 1-(2,6-dichlorobenzoyl)-2-formyl-, and 1-(phenylsulfonyl)pyrroles with palladium acetate and alkyl acrylates gave the corresponding α-alkenyl-substituted pyrroles in good yields, while the reaction of 1-(2,6-dichlorobenzoyl)-2,5-dimethylpyrrole gave small amounts of β-alkenyl-substituted pyrroles.Under similar conditions, 1-(2,6-dichlorobenzoyl)pyrazole and 1-(2,6-dichlorobenzoyl)-3,5-dimethylpyrazole reacted with palladium acetate and alkyl acrylates to give the corresponding 4-alkenyl-substituted pyrazoles.The reaction of 1-(2,6-dichlorobenzoyl)-4-methylpyrazole gave 5-alkenyl-substituted pyrazole.
