284491-66-3Relevant articles and documents
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.
Bridging amines with CO2: Organocatalyzed reduction of CO2 to aminals
Frogneux, Xavier,Blondiaux, Enguerrand,Thuéry, Pierre,Cantat, Thibault
, p. 3983 - 3987 (2015/11/11)
The four-electron reduction of CO2 in the presence of secondary aromatic amines is described for the first time to access aminals. Under metal-free hydrosilylation conditions, the four C-O bonds of CO2 are cleaved, and the organocatalysts are able to balance the reactivity of CO2 to promote the selective formation of two C-N and two C-H bonds. The methodology enables the formation of various symmetrical and unsymmetrical aminals.
Mn(ii) acetate: An efficient and versatile oxidation catalyst for alcohols
Raeisaenen, Minna T.,Al-Hunaiti, Afnan,Atosuo, Elisa,Kemell, Marianna,Leskelae, Markku,Repo, Timo
, p. 2564 - 2573 (2014/07/22)
A homogeneous catalytic system consisting of Mn(ii) acetate (18 μmol), tert-butylhydroperoxide (2.5 mmol), acetonitrile (1.5 mL) and trifluoroacetic acid (91 μmol) was developed for efficient and selective oxidation of various alcohols (1 mmol). The system yielded good to quantitative conversions (42-100%) of various secondary alcohols, such as 2-octanol, fenchyl alcohol and borneol, to their corresponding ketones. Primary alcohols, for example 1-octanol and differently substituted benzyl alcohols, were mainly converted to their corresponding carboxylic acids. Studies with a selection of hydrocarbons, tertiary amines and a cyclic ether isochroman showed that besides alcohols, other substrates can be oxidised as well.
Surprising formylations with methylformamidopyridines and oxalyl chloride
Cheng, Ying,Liu, Qing-Xiang,Meth-Cohn, Otto
, p. 3475 - 3478 (2007/10/03)
4-N-(Methylformamido)pyridine with (COCl)2 gives the corresponding Vilsmeier reagent which reacts with 4-substituted dimethylanilines to produce 5-substituted-N-methylisatins. The corresponding 2-N- (methylformamido)pyridine under the same conditions generates benzo[2,3]pyrido[6,7-b][1,5]diazocines. (C) 2000 Elsevier Science Ltd.
