10385-30-5Relevant articles and documents
In situ generation of o-lodoxybenzoic acid (IBX) and the catalytic use of it in oxidation reactions in the presence of oxone as a co-oxidant
Thottumkara, Arun P.,Bowsher, Michael S.,Vinod, Thottumkara K.
, p. 2933 - 2936 (2005)
(Chemical Equation Presented) Catalytic use of o-iodoxybenzoic acid (IBX) in the presence of Oxone as a co-oxidant is demonstrated for the oxidation of primary and secondary alcohols in user- and eco-friendly solvent mixtures. Also demonstrated is the in situ (re)oxidation of 2-iodosobenzoic acid (IBA) and even commercially available 2-iodobenzoic acid (2IBAcid) by Oxone to IBX allowing one to use these less hazardous reagents, in place of potentially explosive IBX, as catalytic oxidants.
Electrostatic complexation and photoinduced electron transfer between Zn-Cytochrome c and polyanionic fullerene dendrimers
Braun, Martin,Atalick, Stefan,Guldi, Dirk M.,Lanig, Harald,Brettreich, Michael,Burghardt, Stephan,Hatzimarinaki, Maria,Ravanelli, Elena,Prato, Maurizio,Van Eldik, Rudi,Hirsch, Andreas
, p. 3867 - 3875 (2003)
Two dendritic fullerene (DF) monoadducts, 2 and 3, which can carry up to 9 and 18 negative charges, respectively, were examined with respect to electrostatic complexation with Cytochrome c (Cytc). To facilitate comprehensive photophysical investigations,
Suppressing carboxylate nucleophilicity with inorganic salts enables selective electrocarboxylation without sacrificial anodes
Corbin, Nathan,Lazouski, Nikifar,Manthiram, Karthish,Steinberg, Katherine,Yang, Deng-Tao
, p. 12365 - 12376 (2021/10/08)
Although electrocarboxylation reactions use CO2as a renewable synthon and can incorporate renewable electricity as a driving force, the overall sustainability and practicality of this process is limited by the use of sacrificial anodes such as magnesium and aluminum. Replacing these anodes for the carboxylation of organic halides is not trivial because the cations produced from their oxidation inhibit a variety of undesired nucleophilic reactions that form esters, carbonates, and alcohols. Herein, a strategy to maintain selectivity without a sacrificial anode is developed by adding a salt with an inorganic cation that blocks nucleophilic reactions. Using anhydrous MgBr2as a low-cost, soluble source of Mg2+cations, carboxylation of a variety of aliphatic, benzylic, and aromatic halides was achieved with moderate to good (34-78%) yields without a sacrificial anode. Moreover, the yields from the sacrificial-anode-free process were often comparable or better than those from a traditional sacrificial-anode process. Examining a wide variety of substrates shows a correlation between known nucleophilic susceptibilities of carbon-halide bonds and selectivity loss in the absence of a Mg2+source. The carboxylate anion product was also discovered to mitigate cathodic passivation by insoluble carbonates produced as byproducts from concomitant CO2reduction to CO, although this protection can eventually become insufficient when sacrificial anodes are used. These results are a key step toward sustainable and practical carboxylation by providing an electrolyte design guideline to obviate the need for sacrificial anodes.
Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 10913 - 10917 (2020/05/25)
A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.
Asymmetric total synthesis method of sex pheromone (R, Z)-21-methyl-8-tripentadecene of psacothea hilaris
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Paragraph 0048; 0059, (2020/12/30)
The invention discloses an asymmetric total synthesis method of sex pheromone (R, Z) 21-methyl-8-tripentadecene of psacothea hilaris, the method comprises the following steps: by using a compound 14 as an initial raw material, assembling a molecular carbon chain according to the sequence of C5+C12+C11+C8; firstly carrying out Wittig reaction with C12 quaternary phosphonium salt, and then carryingout another Wittig reaction and catalytic hydrogenation to obtain the key intermediate (R)-13-methylheptanoic acid-1-alcohol. Finally, after primary oxidation and Wittig reaction, obtaining the sex pheromone of the psacothea hilaris, wherein the total yield is 36.2%. According to the invention, the problems of lengthy synthesis steps, difficult resolution and low yield of non-chiral raw materialsin chiral pheromone synthesis are solved, and the asymmetric total synthesis of the sex pheromone (R,Z)21-methyl-8-tripentadecene of psacothea hilaris is completed. The method has the advantages of high yield, simple and convenient chemical operation and competitiveness in the aspect of cost control.
