103-41-3Relevant articles and documents
Synthesis of benzyl esters using 2-benzyloxy-1-methylpyridinium triflate
Tummatorn, Jumreang,Albiniak, Philip A.,Dudley, Gregory B.
, p. 8962 - 8964 (2007)
(Chemical Equation Presented) Triethylamine (Et3N) mediates esterification reactions between the title reagent (1) and carboxylic acids. Alcohols, phenols, amides, and other sensitive functionality are not affected; a dual role for Et3N as a promoter and a scavenger is postulated. Benzyl esters are obtained from substrates including amino acid and sugar derivatives.
Efficient Method for the Preparation of Primary, Inverted Secondary and Tertiary Alkyl Carboxylates from Alcohols and Carboxylic Acids by a New Type of Oxidation-Reduction Condensation Using Simple 1,4-Benzoquinone
Shintou, Taichi,Mukaiyama, Teruaki
, p. 1100 - 1101 (2003)
A new type of oxidation-reduction condensation using in situ formed alkoxydiphenylphosphines (i.e., diphenylphosphinite esters), easily available 1,4-benzoquionone and carboxylic acids provides a new and efficient method for the preparation of alkyl carboxylates from the corresponding alcohols under mild and neutral conditions. Further, the yields of the corresponding inverted carboxylates were equally high in the case of chiral secondary or tertiary alcohols.
METAL-CATALYZED SYNTHESIS OF CARBOXYLIC ESTERS UTILIZING (E)-PHENYL 2-PYRIDYL KETONE O-ACYLOXIMES (PPAO)
Miyasaka, Tadayo,Ishizu, Hidehiro,Sawada, Akihiro,Fujimoto, Akiko,Noguchi, Shunsaku
, p. 871 - 874 (1986)
(E)-Phenyl 2-pyridyl ketone O-acyloximes (PPAO) could be highly activated by metal ions such as Fe(3+), Cu(2+), and Zn(2+), and the most effective catalyst for the synthesis of carboxylic esters was found to be Zn(2+).Furthermore, sterically hindered carboxylic esters were easily obtained utilizing PPAOs and alcoholates in high yields.
Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions
Mou, Fen,Sun, Yadong,Jin, Weiwei,Zhang, Yonghong,Wang, Bin,Liu, Zhiqing,Guo, Lei,Huang, Jianbin,Liu, Chenjiang
, p. 23041 - 23045 (2017)
A metal-free protocol for the direct oxidative esterification of the Csp3-H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.
A simple one-pot organometallic formylation/trapping sequence using N-formylcarbazole
Dixon, Darren J.,Lucas, Amanda C.
, p. 1092 - 1094 (2004)
Treatment of a range of sp3-, sp2- and sp-nucleophiles with N-formyl carbazole leads to the formation of the metastable anionic carbazole carbinols. In the presence of a second nucleophilic reagent such as phosphonoacetate or an organolithium, these collapse on warming to the aldehyde which is trapped in situ to afford the α,β-unsaturated esters or secondary carbinols respectively.
Palladium(II)@Zirconium-Based Mixed-Linker Metal–Organic Frameworks as Highly Efficient and Recyclable Catalysts for Suzuki and Heck Cross-Coupling Reactions
Sun, Rong,Liu, Bing,Li, Bo-Geng,Jie, Suyun
, p. 3261 - 3271 (2016)
Two series of amine-functionalized Zr-based mixed-linker metal–organic frameworks (MOFs; UiO-66-Mix and UiO-67-Mix) have been synthesized with different ratios of 1,4-benzenedicarboxylate/2-amino-1,4-benzenedicarboxylate and 4,4′-biphenyldicarboxylic acid/2-amino-biphenyl-4,4′-dicarboxylic acid incorporated into their structures. The pendant amino groups were postmodified by the condensation reaction with pyridine-2-carboxaldehyde, and Pd metal centers were anchored onto the MOFs by coordination to the pyridylimine moieties. The two series of heterogeneous Pd catalysts (UiO-66-Mix-PI-Pd and UiO-67-Mix-PI-Pd) were utilized for the Suzuki and Heck cross-coupling reactions in ethanol/water under mild reaction conditions and they showed a remarkably high catalytic activity. The porosity of the MOFs and the density of the metal binding sites of the Pd catalysts had great influence on the Suzuki and Heck cross-coupling reactions. The best results were achieved with a very low Pd loading (0.054 mol %), and the use of UiO-67-3-PI-Pd catalyst led to the complete conversion of reaction substrates. Moreover, the catalysts were readily recovered and recycled in at least 10 cycles without significant leaching or loss of catalytic activity. The catalysts were generally applicable for different reaction substrates with various substituents in both Suzuki and Heck reactions.
Protonation of homoenolate equivalents generated by N-heterocyclic carbenes
Maki, Brooks E.,Chan, Audrey,Scheidt, Karl A.
, p. 1306 - 1315 (2008)
Homoenolate equivalents are generated by Lewis basic N-heterocyclic carbene catalysts and then protonated to generate efficiently saturated esters from unsaturated aldehydes. This reactivity is extended to the generation of β-acylvinyl anions from alkynyl aldehydes. The asymmetric protonation of a homoenolate equivalent generated from a β,β-disubstituted aldehyde can be accomplished with a chiral N-heterocyclic carbene. Georg Thieme Verlag Stuttgart.
An Effective Pt-Cu/SiO2 Catalyst for the Selective Hydrogenation of Cinnamaldehyde
Wang, Dong,Zhu, Yujun
, (2018)
The bimetal catalyst Pt-Cu/SiO2 was prepared by the impregnation method. Its catalytic performance was investigated by the selective hydrogenation of cinnamaldehyde. Pt-Cu/SiO2 exhibited much higher selectivity (64.1%) to cinnamyl al
N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions
Grasa, Gabriela A.,Kissling, Rebecca M.,Nolan, Steven P.
, p. 3583 - 3586 (2002)
(graph presented) Imidazol-2-ylidenes, a family of N-heterocyclic carbones (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl-or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.
Selective hydrogenation of cinnamaldehyde to cinnamal alcohol over platinum/graphene catalysts
Ji, Xiwang,Niu, Xiaoyu,Li, Bo,Han, Qing,Yuan, Fulong,Zaera, Francisco,Zhu, Yujun,Fu, Honggang
, p. 3246 - 3253 (2014)
Catalysts made of Pt nanoparticles dispersed on graphene (X wt%Pt/G, X=2.0, 3.5, and 5.0) were prepared and characterized by XRD, Raman spectroscopy, BET surface area measurements, TEM, and X-ray photoelectron spectroscopy (XPS), and a 3.5 wt% Pt supported on Vulcan Carbon catalyst (3.5 wt%Pt/VC) was included as a reference. Although the mean Pt nanoparticle size is approximately 4.4 nm for all X wt%Pt/G and 3.5 wt%Pt/VC catalysts, cinnamal alcohol was produced with high selectivity only with the graphene-supported catalysts: 92% conversion and 88% selectivity toward cinnamal alcohol were obtained with 3.5 wt%Pt/G. This catalyst also showed good stability in recycling tests. The good selectivity observed with the graphene-based catalysts is attributed to the higher fraction of reduced surface Pt0 atoms seen on the surface of the Pt nanoparticles (determined by XPS). This interpretation is consistent with DFT calculations. Additional π -π interactions between cinnamaldehyde and graphene may also play a role in the selective hydrogenation of cinnamaldehyde.
