59746-67-7Relevant academic research and scientific papers
Cobalt-catalyzed aminocarbonylation of (hetero)aryl halides promoted by visible light
Alexanian, Erik J.,Veatch, Alexander M.
, p. 7210 - 7213 (2020/07/23)
The catalytic aminocarbonylation of (hetero)aryl halides is widely applied in the synthesis of amides but relies heavily on the use of precious metal catalysis. Herein, we report an aminocarbonylation of (hetero)aryl halides using a simple cobalt catalyst under visible light irradiation. The reaction extends to the use of (hetero)aryl chlorides and is successful with a broad range of amine nucleophiles. Mechanistic investigations are consistent with a reaction proceeding via intermolecular charge transfer involving a donor-acceptor complex of the substrate and cobaltate catalyst.
Copper-Catalyzed Carbonylative Cross-Coupling of Arylboronic Acids with N-Chloroamines for the Synthesis of Aryl Amides
Yin, Zhiping,Wang, Zechao,Li, Wanfang,Wu, Xiao-Feng
, p. 1769 - 1772 (2017/04/13)
A novel copper-catalyzed carbonylative cross-coupling between N-chloroamines and arylboronics acids has been developed. With copper(I) oxide as the catalyst, various desired amide compounds were produced in moderate to good yields. Functional groups such as iodide and alkene are tolerated. Notably, this is the first example of a copper-catalyzed aminocarbonylation with N-chloroamines.
Palladium-Catalyzed Carbonylative Synthesis of Amides from Aryltriazenes under Additive-Free Conditions
Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
supporting information, p. 3992 - 3995 (2017/07/28)
An interesting palladium-catalyzed carbonylative synthesis of amides from aryltriazenes was developed. By using Pd(MeCN2)Cl2 as the catalyst precursor under CO pressure through a N2 extrusion/CO insertion sequence, a broad range of aryltriazenes were transformed into the corresponding amides in good yields with excellent functional group tolerance. Remarkably, no additives such as acids or phosphine ligands were required.
Aerobic oxidative amidation of aromatic and cinnamic aldehydes with secondary amines by CuI/2-pyridonate catalytic system
Zhu, Mingwen,Fujita, Ken-Ichi,Yamaguchi, Ryohei
, p. 9102 - 9109,8 (2012/12/11)
A simple and convenient CuI/2-pyridonate catalytic system for the oxidative amidation of aldehydes with secondary amines has been developed. With this system, a variety of useful arylamides have been synthesized in moderate to good yields in the presence of small amount of copper catalyst and the pyridonate ligand, generating only water as a coproduct. Synthesis of cinnamamides was also achieved by the reactions of cinnamaldehydes with secondary amines in moderate yields. Air was successfully employed as a green oxidant in this catalytic system, achieving a safe and atom-efficient system for the synthesis of amides.
Aminolysis of S-4-nitrophenyl X-substituted thiobenzoates: Effect of nonleaving-group substituents on reactivity and mechanism
Im, Li-Ra,Jeon, Sang-Eun,Um, Ik-Hwan
, p. 1153 - 1157 (2011/11/12)
A kinetic study is reported for aminolysis of S-4-nitrophenyl X-substituted thiobenzoates 3a-g in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. Thiol esters 3a-g are 7.8-47.6 fold more reactive than the corresponding oxygen esters (i.e., 4-nitrophenyl X-substituted benzoates 1a-g). Such reactivity order appears to be in accordance with the expectation that 4-nitrothiophenoxide in 3a-g is a better nucleofuge than 4-nitrophenoxide in 1a-g since the former is 2.64 pKa units less basic than the latter. Hammett plot for the reactions of 3a-g exhibit poor correlation coefficients (R2 = 0.977-0.986) with negative deviation by substrates possessing an electrondonating group (EDG), while the Yukawa-Tsuno plots result in excellent linear correlation (R2 = 0.995-0.997) with ? = 0.93-1.23 and r = 0.57-0.67, indicating that the negative deviation shown by substrates possessing an EDG is caused by ground-state stabilization through resonance interactions but not due to a change in ratedetermining step upon changing the nonleaving-group substituent X. The p value increases as the incoming amine becomes more basic and more reactive, indicating that the RSP is not operative in the current reactions.
