146767-39-7Relevant academic research and scientific papers
Palladium-catalyzed mono-α-arylation of carbonyl-containing compounds with aryl halides using dalphos ligands
Crawford, Sarah M.,Alsabeh, Pamela G.,Stradiotto, Mark
, p. 6042 - 6050,9 (2020/09/02)
We report the extension and optimization of the [Pd(cinnamyl)Cl] 2/DalPhos catalyst system, previously found effective for the mono-α-arylation of acetone, to the mono-α-arylation of a variety of carbonyl-containing compounds with aryl halides and heteroaryl halides. Aryl methyl ketones, heteroaryl methyl ketones, propiophenones, malonates, and methoxyacetone can be α-arylated under relatively mild conditions and in good yields. We also report the limitations of the ligand/catalyst system towards other classes of carbonyl-containing compounds. We report the application of the [Pd(cinnamyl)Cl]2/DalPhos catalyst system, previously found effective for the mono-α-arylation of acetone, to the mono-α-arylation of a variety of carbonyl-containing compounds with aryl halides and heteroaryl halides.
One-pot synthesis of useful heterocycles in medicinal chemistry using a cascade strategy
Wu, Guiyong,Yin, Weiyu,Shen, Hong C.,Huang, Yong
supporting information; experimental part, p. 580 - 585 (2012/04/23)
To access useful heterocycles in medicinal chemistry such as pyridazinones, dihydropyrimidinones, and dihydropyrimidinthiones, a "green" mild and highly efficient one-pot triple cascade was developed involving a Claisen-decarboxylation, electrophilic reaction, and subsequent heterocyclization. In addition, indazoles and benzofurans could also be constructed via a double cascade. To develop the cascade process, a direct Claisen-decarboxylation reaction was firstly optimized. This reaction can then couple with electrophilic reactions including alkylation, Michael addition or aldol reaction to enable the preparation of various aryl ketones in a one-pot fashion. The Royal Society of Chemistry 2012.
A new method of synthesizing deoxybenzoins from 1,3-dimethyl-2-(α- benzyloxybenzyl)imidazolium and 1,3-dimethyl-2-(α- benzyloxybenzyl)benzimidazolium iodides based on Wittig-type rearrangement
Miyashita, Akira,Matsuoka, Yoshiyuki,Suzuki, Yumiko,Iwamoto, Ken-Ichi,Higashino, Takeo
, p. 1235 - 1242 (2007/10/03)
The treatment of 1,3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides 1 with a base gave deoxybenzoins 2 in moderate yields. Sodium hydride (NaH), potassium carbonate (K2CO3), and cesium carbonate (Cs2CO3) were effective bases in this reaction. Deoxybenzoins 2 were produced through rearrangement of the benzyl group followed by expulsion of the 1,3- dimethylbenzimidazolium ylide (A). The rearrangement proceeds in a way similar to Wittig rearrangement. Deoxybenzoins 2 were also formed in good yields from 1,3-dimethyl-2-(α-benzyloxybenzyl)imidazolium iodides 4 upon similar treatment. However, the quaternary salts having a thiazolium moiety 5a and a pyridinium moiety 6a failed to produce deoxybenzoin (2a).
α-arylation vs. α-arylhydrazonylation of alkyl aryl ketones with arylazo tert-butyl sulfides
Dell'Erba,Novi,Petrillo,Tavani
, p. 235 - 242 (2007/10/02)
Potassium enolates of alkyl aryl ketones react selectively in DMSO with phenylazo 1a and 4-methylphenylazo tert-butyl sulfide 1b undergoing respectively effective α-phenylation via S(RN)1 and α-(4-methylphenyl)hydrazonylation via elimination-addition.
