53698-52-5Relevant academic research and scientific papers
Small organic molecules with tailored structures: Initiators in the transition-metal-free C-H arylation of unactivated arenes
Chen, Suqing,Chen, Wenjun,Chen, Yu,Liu, Zhenghui,Mu, Tiancheng,Wang, Peng,Yan, Zhenzhong
, p. 14500 - 14509 (2020/04/27)
Simple, small organic molecules containing nitrogen and oxygen atoms in their structures have been disclosed to catalyze transition-metal-free C-H arylation of unactivated arenes with aryl iodides in the presence of tBuOK. In this article, an optimized catalytically active molecule, (2-(methylamino)phenyl)methanol, was designed. A broad range of aryl iodides could be converted into the corresponding arylated products at 100 °C over 24 h with good to excellent yields. Mechanistic experiments verified that radicals participated in this catalytic transformation and that the cleavage of the aromatic C-H bond was not the rate determining step. A K+ capture experiment by 18-crown-6 emphasized the significance of the cation species of the strong base. Fourier transform infrared spectroscopy proved that the catalytic system was activated by the hydrogen bonds between small organic molecules and tBuOK. Also, a clear mechanism was proposed. This transition-metal-free method affords a promising system for efficient and inexpensive synthesis of biaryls via a user-friendly approach, as confirmed by scale-up experiments.
Pd-Catalyzed Ligand-Free Synthesis of Arylated Heteroaromatics by Coupling of N-Heteroaromatic Bromides with Iodobenzene Diacetate, Iodosobenzene, or Diphenyliodonium Salts
Wang, Xiajun,He, Yongqin,Ren, Mengdan,Liu, Shengkang,Liu, He,Huang, Guosheng
, p. 7958 - 7962 (2016/09/09)
An efficient method for synthesizing arylated heteroaromatics has been reported via Pd-catalyzed ligand-free cross-coupling of N-heteroaromatic bromides with iodine(III) reagents under mild conditions. Iodobenzene diacetate, iodosobenzene, and diphenyliod
Studies on Pd/NiFe2O4 catalyzed ligand-free Suzuki reaction in aqueous phase: Synthesis of biaryls, terphenyls and polyaryls
Borhade, Sanjay R.,Waghmode, Suresh B.
experimental part, p. 310 - 319 (2011/06/18)
Palladium supported on nickel ferrite (Pd/NiF2O4) was found to be a highly active catalyst for the Suzuki coupling reaction between various aryl halides and arylboronic acids. The reaction gave excellent yields (70-98%) under ligand free conditions in a 1:1 DMF/H2O solvent mixture, in short reaction times (10-60 min). The catalyst could be recovered easily by applying an external magnetic field. The polyaryls were similarly synthesized.
Studies on phosphine free Pd-salen complexes as effective catalysts for aqueous Suzuki reaction
Borhade, Sanjay R.,Waghmode, Suresh B.
experimental part, p. 565 - 572 (2010/12/25)
Palladium complexes of the salen ligands, N,N'-bis(salicylidene)- ethylenediamine and N,N'-bis(salicylidene)-1,.-phenylenediamine have been explored for their catalytic activity in a phosphine-free aqueous Suzuki reaction. The various reaction parameters have been systematically optimized with respect to various solvents, bases, temperatures and Pd concentrations. The studies conclude that 1:1 DMF to water solvent ratio, Na2CO 3 as base and 0.5 mo1% of palladium at 90°C is apt for Suzuki reactions. Rapid transformation of substituted aryl iodides and aryl bromides into corresponding biaryls has been observed with excellent yield ranging from 70-86%, under optimized conditions.
Regioselective synthesis of 2,3-dihydrospiro[1,4]dioxino[2,3-b]pyridine derivatives
Tony, Kurissery A.,Chittimalla, Santhosh Kumar,Abraham Rajkumar,Chakrabarti, Anjan
scheme or table, p. 4350 - 4353 (2010/09/12)
2-Chloropyridines and an aryl bromide underwent palladium-catalyzed intramolecular C-O bond forming reactions to provide 2,3-dihydrospiro[1,4] dioxino[2,3-b]pyridine derivatives and a benzodioxin, regioselectively.
8-Azabicyclo[3.2.1]octane derivatives
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Page/Page column 10-11, (2008/06/13)
The present invention relates to a 8-azabicyclo[3.2.1]octane derivative of Formula I, wherein each of the substituents is given the definition as set forth in the specification and claims, or a pharmaceutically acceptable salt thereof or solvate thereof. The present invention also relates to a pharmaceutical composition comprising an 8-azabicyclo[3.2.1]octane derivative in admixture with one or more pharmaceutically acceptable auxiliaries and to the use of the 8-azabicyclo[3.2.1]octane derivative in therapy.
8-AZABICYCLO[3.2.1]OCTANE DERIVATIVES USEFUL AS MONOAMINE REUPTAKE INHIBITORS
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Page/Page column 23, (2010/11/27)
The present invention relates to a 8-azabicyclo[3.2.1]octane derivative of Formula I, wherein R1 is H or C1-5alkyl; Y is O, S or O(CH2)m; m is 1 or 2; n is 0 or 1; Ar1 is phenylene or pyridylene, said phenylene and pyridylene being 1,3-linked with respect to O and when n is 1 with Y and when n is 0 with Ar2, said phenylene or pyridylene being optionally substituted with one or two substituents independently selected from halogen, C1-5alkyl, C1-5alkoxy, C3-6cycloalkyl, C2-5alkenyl, C2-5alkynyl, phenyl, CN and hydroxy, wherein said C1-5alkyl and C1-5alkoxy are optionally substituted with one to three halogens and wherein the oxygen of said hydroxy is optionally bonded to Ar2 to form a 5-membered ring; Ar2 is phenyl or a 5-6 membered heteroaryl, said phenyl or 5-6 membered heteroaryl being optionally substituted with one to three substituents independently selected from halogen, C1-5alkyl, C1-5alkoxy, CN, CONR2R3, CO2R4, NHCOR5 and hydroxy, wherein said C1-5alkyl and C1-5alkoxy are optionally substituted with one to three halogens and wherein the oxygen of said hydroxy is optionally bonded to Ar1 to form a 5-membered ring; R2-R4 are independently H or C1-5alkyl and R5 is C1-5alkyl, or a pharmaceutically acceptable salt or solvate thereof. The present invention also relates to a pharmaceutical composition comprising a 8- azabicyclo[3.2.1]octane derivative according to the present invention in admixture with one or more pharmaceutically acceptable auxiliaries and to the use of a 8- azabicyclo[3.2.1]octane derivative according to the present invention in therapy.
