1011-47-8Relevant articles and documents
Synthesis of Aryl Methyl Ketones mediated by Cobalt Tetracarbonyl Anion
Miura, Masahiro,Akase, Fumiaki,Nomura, Masakatsu
, p. 241 - 242 (1986)
The reaction of aryl halides with excess of methyl iodide in the presence of cobalt tetracarbonyl anion (generated under phase-transfer conditions), gave aryl ketones along with aromatic carboxylic acids.
Chiral ferrocenyl ligands with bidentate pyridine donors. Synthesis and application in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropenyl-1-esters
Mroczek, Agnieszka,Erre, Giulia,Taras, Rossana,Gladiali, Serafino
, p. 1921 - 1927 (2010)
A synthetic procedure relying on the Friedlaender condensation of enantiopure α-amino ferrocenecarboxaldeyde has been devised for the regio-designed elaboration of a pyridine nucleus fused onto the ferrocene scaffold. Three novel bidentate ligands with different pyridine nitrogen donors featuring the [3,2-b]ferrocenopyridine fragment a as the sole chirogenic element have been prepared in enantiopure form through a multi step route involving the diastereoselective deprotonation of a chiral acetal of ferrocenecarboxaldehyde in the stereodetermining step. The ligands were assessed in the Pd-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl esters with good stereoselectivity.
2-Quinolinecarboxaldehyde: an unusual partner in the Henry reaction and subsequent elimination
Nomland, Ashley,Hills, Ivory D.
, p. 5511 - 5514 (2008)
2-Quinolinecarboxaldehyde participates in a standard Henry reaction when combined with a nitroalkane and catalytic amounts of base. However, water is not readily eliminated from the resulting β-nitro alcohol intermediate to form the expected nitroalkene. Instead, the elimination of nitrous acid is observed furnishing an unexpected ketone product.
Simple and mild method for preparation of α-pyridinecarboxylates and α-pyridyl ketones via trimethylstannyl derivatives
Yamamoto,Ouchi,Tanaka
, p. 1028 - 1030 (1995)
Alkoxycarbonylation and acylation at the α-position of pyridine, quinoline, and isoquinoline via the respective trimethylstannyl derivatives were satisfactorily performed by employing ethyl chloroglyoxylate and acylformyl chloride under mild conditions.
Metal-, Photocatalyst-, and Light-Free Minisci C-H Acetylation of N-Heteroarenes with Vinyl Ethers
Dong, Jianyang,Liu, Jianhua,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 4374 - 4378 (2021/06/21)
Herein, we report a mild, operationally simple method for Minisci C-H acetylation of N-heteroarenes using vinyl ethers as robust, inexpensive acetyl sources. The reactions do not require a conventional photocatalysis, electrocatalysis, metal catalysis, light activation, or high temperature. This method is thus significantly more sustainable than previously reported methods in terms of cost, reagent toxicity, and waste generation. This protocol can be expected to obtain medically relevant molecules from abundant feedstock materials.
Metal-free C-H methylation and acetylation of heteroarenes with PEG-400
Kudale, Vishal Suresh,Wang, Jeh-Jeng
supporting information, p. 3506 - 3511 (2020/06/25)
The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.