5181-06-6Relevant academic research and scientific papers
Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
Chen, Fengyang,Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Zhou, Qifan
, p. 4590 - 4600 (2019/12/11)
In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.
Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime
Yuan, Chunling,Zhang, Lei,Zhao, Yingdai
, (2019/11/28)
We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.
Synthesis of Arylamines via Aminium Radicals
Svejstrup, Thomas D.,Ruffoni, Alessandro,Juliá, Fabio,Aubert, Valentin M.,Leonori, Daniele
, p. 14948 - 14952 (2017/11/20)
Arylamines constitute the core structure of many therapeutic agents, agrochemicals, and organic materials. The development of methods for the efficient and selective construction of these structural motifs from simple building blocks is desirable but stil
Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis
Martin, Anthony R.,Makida, Yusuke,Meiries, Sebastien,Slawin, Alexandra M. Z.,Nolan, Steven P.
supporting information, p. 6265 - 6270 (2013/12/04)
Seven new air- and moisture-stable nickel complexes bearing flexible bulky NHC (N-heterocyclic carbene) ancillary ligands (NHC = IPr, IPrTol, IPrOMe, IPent) are reported. Using experimentally determined crystal structures, the steric
Iron-catalyzed oxidative C(3)-H functionalization of amines
Takasu, Noriaki,Oisaki, Kounosuke,Kanai, Motomu
supporting information, p. 1918 - 1921 (2013/06/04)
Fe-catalyzed direct dehydrogenative C(3)-functionalization of tertiary arylamines was developed via activation of the sp3 C(3)-H bond. The reaction is applicable to both cyclic and acyclic amines. The key process is the catalytic desaturative enamine formation from tertiary amines and position-selective C-C bond formation (addition to nitro olefins) at the β-carbon. Products can be converted to versatile and unique nitrogen-containing molecules.
Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents
Nguyen, Minh H.,Smith, Amos B.
supporting information, p. 4872 - 4875 (2013/10/08)
The development and validation of copper-catalyzed, electrophilic amination of aryl and heteroaryl organolithiums with N,N-dialkyl-O-benzoylhydroxylamines have been achieved exploiting recoverable siloxane transfer agents. Given the ready availability of organolithium compounds, the mild reaction conditions, the ease of product purification, and the ready recovery of the siloxane transfer agents, this transformation comprises a useful tactic to access diverse aryl and heteroaryl amines.
Cobalt-catalyzed electrophilic amination of arylzincs with N-chloroamines
Qian, Xin,Yu, Zailu,Auffrant, Audrey,Gosmini, Corinne
supporting information, p. 6225 - 6229 (2013/07/05)
Roles reversed: An efficient cobalt-catalyzed electrophilic amination of arylzinc reagents has been achieved. A variety of functionalized arylzincs and N-chloroamines were coupled under mild conditions (see scheme). Both secondary and tertiary arylamines were obtained in moderate to excellent yields. Copyright
Cu-Al hydrotalcite: An efficient and reusable ligand-free catalyst for the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines
Sreedhar,Arundhathi,Linga Reddy,Amarnath Reddy,Lakshmi Kantam
experimental part, p. 2517 - 2522 (2010/03/24)
Copper-aluminum hydrotalcite catalysts were effectively used in the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines to afford the corresponding N-alkylated/arylated amines in excellent yields. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles with almost consistent activity. Georg Thieme Verlag Stuttgart.
Aromatic amination of aryl bromides catalysed by copper/β-diketone catalysts: The effect of concentration
De Lange, Ben,Lambers-Verstappen, Marielle H.,Schmieder-Van De Vondervoort, Lizette,Sereinig, Natascha,De Rijk, Ron,De Vries, André H. M.,De Vries, Johannes G.
, p. 3105 - 3109 (2008/02/13)
CuCl ligated with β-diketones were found to be good catalysts for the animation of aryl bromides. Crucial is the concentration of the substrates: at 5 M the rate and selectivity improves substantially. In addition, K 2CO3 can be used as base instead of expensive Cs 2CO3. Primary and secondary amines, heterocycles and anilines could be arylated in good yields. Georg Thieme Verlag Stuttgart.
Cupric acetate mediated N-arylation by arylboronic acids: A preliminary investigation into the scope of application
Cundy, Darren J.,Forsyth, Stewart A.
, p. 7979 - 7982 (2007/10/03)
A range of NH substrates of varying nucleophilicity were reacted with a selection of electronically diverse aryl boronic acids in the presence of cupric acetate in order to evaluate the generality of a previously described N-arylation procedure. The results of that investigation are discussed.
