15111-14-5Relevant articles and documents
Polyoxometalate catalyzed imine synthesis: Investigation of mechanistic pathways
Adhikary, Subhasis D.,Mandal, Debaprasad
supporting information, (2020/05/25)
The syntheses of imines by oxidative coupling of primary alcohols and amines were achieved by using 2 molpercent polyoxometalate (POM) Na12[WZn3(H2O)2(ZnW9O34)2] (Zn–WZn3) catalyst in the presence of t-BuOK and di-oxygen with excellent conversion (up to 100percent) and selectivity (up to 100percent). Non-noble metal-based POM catalyst in the presence of base represents a new reaction protocol for the selective synthesis of imine from both aromatic and aliphatic primary amines with functional group tolerance. Control experiment shows the formation of di-oxygen bind Zn–WZn3 activated species. The electron-density of POM is mostly situated on the surface oxygen atoms of W–O–W bonds which can engage the alcoholic OH group and helps for the imine selectivity in the second step of imine synthesis.
Diastereoselective Nickel-Catalyzed Carboiodination Generating Six-Membered Nitrogen-Based Heterocycles
Marchese, Austin D.,Kersting, Louise,Lautens, Mark
supporting information, p. 7163 - 7168 (2019/09/12)
A scalable, diastereoselective nickel-catalyzed carboiodination reaction is reported that avoids metal-based reducing agents. Novel anti-dihydroquinolones and previously unreported tetrahydroquinolines are now readily prepared. The generation of anti-dihydroquinolones is noteworthy, as this selectivity is opposite to that of the Pd variant. Mechanistic insight into the nature of the nickel-catalyzed carboiodination reaction was derived experimentally, suggesting a catalyst-controlled cyclization and stereoretentive reductive elimination.
Microwave-Assisted Nickel-Catalyzed Synthesis of Benzimidazoles: Ammonia as a Cheap and Nontoxic Nitrogen Source
Ke, Fang,Zhang, Peng,Xu, Yiwen,Lin, Xiaoyan,Lin, Jin,Lin, Chen,Xu, Jianhua
, p. 2722 - 2726 (2018/12/14)
An efficient and convenient Ni-catalyzed C-N bond formation for the synthesis of various benzimidazoles from various 2-haloanilines, aldehydes, and ammonia in a concise manner is reported. This protocol uses commercially available, nonhazardous, clean ammonia as a reaction partner instead of other nitrogen sources. Benzimidazoles, as the sole products, were obtained in high to excellent yields (up to 95%).
Synthesis of benzimidazoles by Cul-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde in water
Ke, Fang,Zhang, Peng,Lin, Chen,Lin, Xiaoyan,Xu, Jianhua,Zhou, Xiangge
, p. 8090 - 8094 (2018/11/23)
An efficient copper-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde for the synthesis of benzimidazoles with 1,10-phenanthroline as the ligand has been developed. A variety of substituted benzimidazole derivatives can be obtained in yields up to 95%.
Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides
Senadi, Gopal Chandru,Wang, Ji-Qi,Gore, Babasaheb Sopan,Wang, Jeh-Jeng
supporting information, p. 2747 - 2753 (2017/08/23)
An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo
A Palladium-Catalyzed Double Carbonylation Approach to Isatins from 2-Iodoanilines
Laursen, Simon R.,Jensen, Mikkel T.,Lindhardt, Anders T.,Jacobsen, Mikkel F.,Skrydstrup, Troels
supporting information, p. 1881 - 1885 (2016/05/09)
A high-yielding procedure for the synthesis of isatins has been developed. Sequential Pd-catalyzed double carbonylation of 2-iodoanilines with near stoichiometric amounts of CO followed by acid-promoted cyclization readily affords an array of isatins. The conversion of 2-iodoanilines to isatins in good to excellent yields was found to proceed with good functional group tolerance. This protocol proved adaptable to 13C-isotope labeling of isatins, which was extended to the synthesis of the 13C-isotope labeled antiviral drug metisazone and the experimental anti-schizophrenia drug ML137.
Lanthanides Mediated Oxidative Cross Coupling of Benzylalcohol and Various Amines to Form Corresponding Imines
Bhattacharjee, Jayeeta,Sachdeva, Mitali,Panda, Tarun K.
supporting information, p. 937 - 940 (2016/09/03)
Herein, a new and efficient approach towards the oxidative cross-coupling of benzylalcohol and various aromatic amines to form corresponding imines with high degree conversion (>80 %) and chemo-selectivity using lanthanide salts as pre-catalysts is presented. The catalyzed oxidative cross-coupling reaction using La(NO3)3·6H2O as pre-catalyst displayed a broad substrate scope. The reaction afforded various substituted imines from the reaction of benzylalcohol with ample variety of amines in good yields.
Copper-catalyzed three-component one-pot synthesis of substituted 2-aryl-1,3-benzoselenazoles
Su, Tao,Xie, Shishun,Li, Bifu,Yan, Jun,Huang, Ling,Li, Xingshu
supporting information, p. 215 - 220 (2015/03/03)
A simple copper-catalyzed, one-pot synthesis of 2-aryl-1,3-benzoselenazole derivatives was developed using inexpensive, readily available 2-iodoanilines, selenium powder, and aromatic aldehydes as the starting materials. The mild reaction conditions and simple procedure without ligands and other additives make this methodology an alternative for preparing these potential selenium-containing compounds very conveniently.
A new synthesis of indoles via intramolecular cyclization of ?-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
Chen, Yan-Yan,Chen, Jia-Hua,Zhang, Niu-Niu,Ye, Lin-Miao,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 478 - 481 (2015/03/05)
2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ?-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-
A new synthesis of indoles via intramolecular cyclization of ο-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
Chen, Yan-Yan,Chen, Jia-Hua,Zhang, Niu-Niu,Ye, Lin-Miao,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 478 - 481 (2015/04/27)
2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ο-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-
