19756-72-0Relevant articles and documents
Nickel-Catalyzed Esterification of Amides Under Mild Conditions
Li, Jun-Fei,Wang, Yao-Fang,Wu, Yuan-Yuan,Liu, Wen-Jing,Wang, Jun-Wen
, p. 874 - 880 (2019/11/13)
Abstract: The use of ligands to adjust the catalytic activity of the catalyst for esterification of amides is challenge in organic chemistry. In this paper, Nickel(II)-NHC-catalyzed the esterification reaction between N,N-di-Boc amide and alcohols at room temperature have been demonstrated. The imidazolium salt bearing a hydroxyl functionalized side arm showed high effective catalytic activity in the activation of the amide N–C bond in air atmosphere. Graphic Abstract: [Figure not available: see fulltext.].
Innovative Multipodal Ligands Derived from Tr?ger's Bases for the Sensitization of Lanthanide(III) Luminescence
Barja, Beatriz C.,Bruttomesso, Andrea C.,Eliseeva, Svetlana V.,Petoud, Stéphane,Ramírez, Javier A.,Trupp, Leandro,Vardé, Mariana
supporting information, p. 16900 - 16909 (2020/11/30)
Herein, the synthesis and characterization of the first family of multipodal ligands with a Tr?ger's base framework designed for the preparation of luminescent lanthanide(III) complexes are reported. Eight ligands were designed and synthesized using diffe
A fast and practical synthesis of tert-butyl esters from 2-tert-butoxypyridine using boron trifluoride·diethyl etherate under mild conditions
La, Minh Thanh,Kim, Hee-Kwon
, p. 3748 - 3754 (2018/05/28)
A practical direct preparation of tert-butyl esters from 2-tert-butoxypyridine has been developed. This system features the use of boron trifluoride·diethyl etherate in toluene solvent to rapidly achieve the reaction at room temperature. Using this reaction protocol, a variety of tert-butyl esters were synthesized from several different carboxylic acids at high yields. This practical procedure provides a promising and effective approach to the protection of carboxylic acids with a tert-butyl group.
Super electron donor-mediated reductive transformation of nitrobenzenes: A novel strategy to synthesize azobenzenes and phenazines
Nozawa-Kumada, Kanako,Abe, Erina,Ito, Shungo,Shigeno, Masanori,Kondo, Yoshinori
supporting information, p. 3095 - 3098 (2018/05/22)
The transformation of nitrobenzenes into azobenzenes by pyridine-derived super electron donor 2 is described. This method provides an efficient synthesis of azobenzenes because of not requiring the use of expensive transition-metals, toxic or flammable reagents, or harsh conditions. Moreover, when using 2-fluoronitrobenzenes as substrates, phenazines were found to be obtained. The process affords a novel synthesis of phenazines.
Mild alkaline hydrolysis of hindered esters in non-aqueous solution
Theodorou, Vassiliki,Alagiannis, Michalis,Ntemou, Nikoleta,Brentas, Alexios,Voulgari, Pinelopi,Polychronidou, Vasiliki,Gogou, Marina,Giannelos, Marios,Skobridis, Konstantinos
, p. 308 - 319 (2018/11/26)
Sterically hindered esters of carboxylic acids, which are considered very resistant to saponification, were rapidly and efficiently saponified in a non-aqueous medium using NaOH in MeOH/CH2Cl2 (1:9) at room temperature. Furthermore, this reaction protocol was extended and successfully applied to the hydrolysis of tosylates and N-tosyl indoles.
Metal-free radical aromatic carbonylations mediated by weak bases
Koziakov, Denis,Jacobi Von Wangelin, Axel
, p. 6715 - 6719 (2017/08/22)
We report a new method of metal-free alkoxycarbonylation. This reaction involves the generation of aryl radicals from arenediazonium salts by a very weak base (HCO2Na) under mild conditions. Subsequent radical trapping with carbon monoxide and alcohols gives alkyl benzoates. The conditions (metal-free, 1 equiv. base, MeCN, r.t., 3 h) tolerate various functional groups (I, Br, Cl, CF3, SF5, NO2, ester). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism.
Metal-free carbonylations by photoredox catalysis
Majek, Michal,Von Wangelin, Axel Jacobi
supporting information, p. 2270 - 2274 (2015/02/19)
The synthesis of benzoates from aryl electrophiles and carbon monoxide is a prime example of a transition-metalcatalyzed carbonylation reaction which is widely applied in research and industrial processes. Such reactions proceed in the presence of Pd or Ni catalysts, suitable ligands, and stoichiometric bases. We have developed an alternative procedure that is free of any metal, ligand, and base. The method involves a redox reaction driven by visible light and catalyzed by eosin Y which affords alkyl benzoates from arene diazonium salts, carbon monoxide, and alcohols under mild conditions. Tertiary esters can also be prepared in high yields. DFT calculations and radical trapping experiments support a catalytic photoredox pathway without the requirement for sacrificial redox partners.
Ultrasound assisted direct oxidative esterification of aldehydes and alcohols using graphite oxide and Oxone
Mirza-Aghayan, Maryam,Zonoubi, Somayeh,Molaee Tavana, Mahdieh,Boukherroub, Rabah
, p. 359 - 364 (2014/10/16)
A sonochemical procedure for direct oxidative esterification of aldehydes and alcohols using graphite oxide and Oxone in an alcoholic solvent is described. Mild reaction conditions, short reaction times, cost-effectiveness, and facile isolation of the products make the present system as a practical method.
Base-free oxidation of alcohols to esters at room temperature and atmospheric conditions using nanoscale Co-based catalysts
Zhong, Wei,Liu, Hongli,Bai, Cuihua,Liao, Shijun,Li, Yingwei
, p. 1850 - 1856 (2015/03/14)
The direct oxidation of alcohols to esters with molecular oxygen is an attractive and crucial process for the synthesis of fine chemicals. To date, the heterogeneous catalyst systems that have been identified are based on noble metals or have required the addition of base additives. Here, we show that Co nanoparticles embedded in nitrogen-doped graphite catalyze the aerobic oxidation of alcohols to esters at room temperature under base-free and atmospheric conditions. Our Co@C-N catalytic system features a broad substrate scope for aromatic and aliphatic alcohols as well as diols, giving their corresponding esters in good to excellent yields. This apparently environmentally benign process provides a new strategy with which to achieve selective oxidation of alcohols.
Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides: Efficient synthesis of esters of tertiary alcohols
Zhu, Yefeng,Wei, Yunyang
, p. 13668 - 13670 (2013/08/23)
Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides has been developed. This protocol affords a novel approach for the synthesis of carboxylic esters of tertiary alcohols under mild conditions. Depending on the catalyst system, a variety of tertiary esters were produced in good to excellent yields.