109575-08-8Relevant academic research and scientific papers
Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation
Marquise, Nada,Harford, Philip J.,Chevallier, Floris,Roisnel, Thierry,Dorcet, Vincent,Gagez, Anne-Laure,Sablé, Sophie,Picot, Laurent,Thiéry, Valérie,Wheatley, Andrew E.H.,Gros, Philippe C.,Mongin, Florence
, p. 10123 - 10133 (2013/11/06)
The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6- tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents.
Deprotonative metalation of aromatic compounds by using an amino-based lithium cuprate
Nguyen, Tan Tai,Marquise, Nada,Chevallier, Floris,Mongin, Florence
experimental part, p. 10405 - 10416 (2011/10/12)
Deprotonative cupration of aromatic compounds by using amino-based lithium cuprates was optimized with 2,4-dimethoxypyrimidine and 2-methoxypyridine as the substrates and benzoyl chloride as the electrophile. [(tmp)2CuLi] (+2 LiCl) (tmp=2,2,6,6-tetramethylpiperidino) was identified as the best reagent and its use was extended to anisole, 1,4-dimethoxybenzene, other substituted pyridines, furan, thiophene and derivatives, and N-Boc-indole (Boc=tert-butyloxycarbonyl). Of the electrophiles employed to attempt the interception of the generated aryl cuprates, aroyl chlorides, iodomethane, and diphenyl disulfide efficiently reacted. In addition, different oxidative agents were identified to afford symmetrical biaryls. Finally, palladium-catalyzed coupling with aryl halides was optimized and allowed the synthesis of different aryl derivatives in medium to good yields.
Synthesis of 4-Amino-3-pyridinyl and 4-Amino-5-pyrimidinyl Aryl Ketones and Related Compounds via an ortho-Lithiation Reaction
Radinov, Rumen,Haimova, Marietta,Simova, Ekaterina
, p. 886 - 891 (2007/10/02)
4-Chloropyridine and 4,6-dichloropyrimidine react regioselectively with lithium diisopropylamide to give 4-chloro-3-lithiopyridine and 4,6-dichloro-5-lithiopyrimidine, respectively.These intermediates react with benzaldehydes to give (4-chloro-3-pyridinyl
