30724-66-4Relevant academic research and scientific papers
Transition-Metal-Free Dehydrogenative N–N Coupling of Secondary Amines with KI/KIO4
Yin, Dehang,Jin, Jian
supporting information, p. 5646 - 5649 (2019/08/21)
A transition-metal-free method for the dehydrogenative N–N coupling of secondary amines has been accomplished. This oxidative KI/KIO4 protocol is mild and operationally simple. A diverse range of diphenylamines, carbazoles, and N-alkylanilines readily undergo N–N homo-coupling effectively. Notably, the N–N cross-coupling of two different arylamines is also demonstrated, which provides a straightforward approach to the complex N–N structures.
Homolytic pathway for the RuO4-oxidation of amines
Florea, Cristina A.,Petride, Horia
, p. 461 - 463 (2019/07/31)
Oxidation by RuO4 of R-NH-Me (R = p-Me-C6H4) gave, in the presence of NaCN, the hydrazine derivative R-NMe-NMe-R as main reaction product. A homolytic Me mechanism is advanced.
NaI-Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants
Fu, Ying,Li, Quan-Zhou,Xu, Qin-Shan,Hügel, Helmut,Li, Ming-Peng,Du, Zhengyin
supporting information, p. 6966 - 6970 (2018/11/23)
A novel NaI-catalyzed oxidative amination of sodium sulfinates, employing both ethylene dibromide (EDB) and air as the oxidants, is described. EDB was first demonstrated to be a promising mild organic oxidant that in air, converted NaI into molecular iodine to promote the cross-coupling reactions of aromatic sodium sulfinates with amines to produce arylsulfonamides. Mechanistic studies indicated that a radical pathway might be involved in the reaction process.
Fast synthesis of hydrazine and Azo derivatives by oxidation of rare-earth-metal-nitrogen bonds
Zhang, Lijun,Xia, Jing,Li, Qinghai,Li, Xihong,Wang, Shaowu
scheme or table, p. 375 - 378 (2011/03/21)
A novel N-N coupling reaction was developed through the oxidation of rare-earth-metal-nitrogen bonds produced by treatment of the easily available rare-earth-metal amides [(Me3Si)2N]3RE(μ-Cl) Li(THF)3 with aromatic primary or secondary amines. The reaction provides the symmetrical or unsymmetrical azo compounds and hydrazine derivatives in good to high yields within a very short time under mild conditions.
A dehydrogenative homocoupling reaction for the direct synthesis of hydrazines from N-alkylanilines in air
Yan, Xue-Ming,Chen, Zhi-Ming,Yang, Fei,Huang, Zhi-Zhen
supporting information; experimental part, p. 569 - 572 (2011/04/22)
A copper-catalyzed N-N bond-forming reaction was performed by a dehydrogenative homocoupling of N-alkylanilines, affording N,N-dialkyl-N,N- diphenylhydrazines in 72-88% yields. This new strategy has the advantages of direct synthesis from N-alkylanilines,
PALLADIUM ASSISTED N-METHYL ACTIVATION OF p-SUBSTITUTED N,N-DIMETHYLANILINES
Sakakibara, Tsutomu,Hamakawa, Tomoko
, p. 1823 - 1824 (2007/10/02)
Intermediates in reaction of N,N-dimethylanilines with palladium(II) acetate were trapped by acetate ion or oxygen to give N-methyloxygenated and demethylated products, while the trapping by other anilines gave homo- and cross-coupling cyclodimers.The reactions proceed via radical cation formation induced by the palladium salt.
Photobenzidine Rearrangements. 6. Mechanism of the Photodecomposition of 1,4-Diaryl-1,4-dialkyl-2-tetrazenes
Bae, Dong-Hak,Shine, Henry J.
, p. 4448 - 4455 (2007/10/02)
The photodecomposition of the tetrazene p-XC6H4N(Me)N=N(Me)NC6H4Y-p (1e,X=Y=Me) in dimethoxyethane (DME) gave 47.4percent of p-XC6H4(Me)NN(Me)C6H4Y-p (2e,X=Y=Me) and 39.6 percent of N-methyl-p-toluidine. When irradiation was carried out in the presence of increasing initial concentrations of n-BuSH, the yield of 2e fell and levelled off at 6percent.Similar experiments in cyclohexane showed that the yield of 2e fell from 45.1percent and leveled off at 10percent.The data indicate that 1e decomposes by a radical pathway and that the 2e is formed partly within and partly outside of a solvent cage. Similar studies with 1d(X=Me, Y=CO2Et) in DME gave three hydrazines: 2d(X=Me,Y=CO2Et) in 13percent and 14.7percent yield, 2e in 7.3percent and 8.0percent yield,and 2f(X=Y=CO2Et) in 14.9percent and 21.2percent yield. The formation of three hydrazines again indicates the formation and intermolecular recombination of methylarylamino radicals. Irradiation of 1d in DME solutions containing n-BuSH caused a fall in the yield of 2e to zero and a leveling off in the yield of 2d to 6percent. The yield of 2f also fell but could not be monitored at high concentrations of n-BuSH because of overlapping high-pressure LC peaks. The results with 1d are also consistent with a cage-recombination process (for 2d) and an intermolecular recombination of radicals (for 2d-f). The methylarylamines p-XC6H4NHMe and p-YC6H4NHMe (X=Me; Y=CO2Et) were also formed from 1d. A sixth product was the bis(arylamino)methane p-YC6H4NHCH2NHC6H4Y-p(4f, Y=CO2Et) in 14-32percent yield (three runs). The origin of 4f is believed to be the disproportionation of radicals p-YC6H4NMe, giving p-YC6H4NHMe and p-YC6H4N=CH2(7f). Hydrolysis of 7f (by small amounts of water in the solvent) to p-YC6H4NH2 (6f) and HCHO followed by addition of 6f to 7f would give 4f. HCHO was found as a volatile product after irradiation. The formation of 4f is further evidence for the formation and intermolecular reaction of arylamino radicals in the photodecomposition of 1,4-dialkyl-1,4-diaryl-2-tetrazenes.
