105669-53-2Relevant academic research and scientific papers
Recyclable Oxofluorovanadate-Catalyzed Formylation of Amines by Reductive Functionalization of CO2 with Hydrosilanes
Wu, Shanxuan,Huang, Zijun,Jiang, Xiaolin,Yan, Fachao,Li, Yuehui,Du, Chen-Xia
, p. 1763 - 1766 (2021/03/01)
An efficient method has been developed for the reductive amination of CO2 by using readily available and recyclable oxofluorovanadates as catalysts. Various amines are transformed into the desired N-formylated products in moderate to excellent yields at room temperature in the presence of phenylsilane. Mechanistic studies based on in situ infrared spectroscopy suggest a reaction pathway initiated through F?Si interactions. The activated phenylsilane allows for CO2 insertion to produce phenylsilyl formate, which undergoes attack by the amine to generate the target product.
Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide
Du, Chen-Xia,Huang, Zijun,Jiang, Xiaolin,Li, Yuehui,Makha, Mohamed,Wang, Fang,Zhao, Dongmei
supporting information, p. 5317 - 5324 (2020/09/17)
We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.
Condensation of Alkanediamines with Formaldehyde; Intramolecular Disproportionation of N-Hydroxymethyl Groups into N-Methyl and N-Formyl Groups
Dale, Johannes,Sigvartsen, Turid
, p. 1064 - 1070 (2007/10/02)
The condensation of α,ω-alkanediamines NH2(CN2)nNH2 with aqueous formaldehyde has been studied by NMR spectroscopy of isolated products and of product mixtures.The condensation was reversible and gave products of widely different types depending on alkane chain length: bicyclic oxadiaza compounds (n = 2, 3, 4), a tricyclic tetraaza compound (n = 2), a quinquecyclic octaaza compound (n = 3), two-dimensional polymers (n = 4, 5).A slow irreversible rearrangement gave in two cases (n = 3, 4), unicyclic 1-formyl-3-methyl-1,3-diaza compounds.The condensation of N,N'-dimethyl-α,ω-alkandediamines CH3NH(CH2)nNHCH3 with aqueous formaldehyde was also studied.The reversible formation of simple unicyclic diaza compounds was observed in all cases (n = 2, 3, 4), but in one case (n = 2) there was again a slow irreversible rearrangement to the N-formyl-N,N'N'-trimethyl derivative.The rearrangement reaction involves a hydride shift and is strictly intramolecular.The conditions for its occurrence can be understood on a conformational basis.
ULTRASOUND IN ORGANIC SYNTHESIS 9 FURTHER RESULTS FOR THE BOUVEAULT REACTION
Einhorn, J.,Luche, J. L.
, p. 1791 - 1792 (2007/10/02)
The Bouveault reaction under ultrasonic irradiation can readily be effected from various amides and the effect of the solvent was studied.In the case of diethylether, results are strongly dependent on the wave frequency.
