5467-99-2Relevant academic research and scientific papers
Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents
Moayyed, Mohammadesmaeil,Saberi, Dariush
, p. 445 - 455 (2020/09/07)
Abstract: Iodine-mediated selective synthesis of β-uramino crotonic esters was achieved via the reaction of β-dicarbonyls and urea at room temperature. Choline chloride/urea mixture, as an eco-friendly, cheap, non-toxic, and recyclable deep eutectic solvent (DES), was employed as sustainable media as well as reagent at the same time in these transformations. Some derivatives of β-uramino crotonic esters were synthesized with good to high yields without a tedious work-up. The process could be done to synthesize the above-mentioned compounds in gram scale. Moreover, oxidative cross-esterification of carboxylic acids with alkyl benzenes was carried out in the above-mentioned DES by the employment of tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant at 80?°C. DES/TBAI system was reused up to five consecutive times. Graphic abstract: Iodine-catalyzed C–N and C–O bond formation in choline chloride/urea as a green solvent under the mild reaction conditions. Providing the clean procedure toward synthesis of β-uramino crotonic esters and benzylic esters.[Figure not available: see fulltext.].
N-Aroylbenzotriazoles as Efficient Reagents for o-Aroylation in Absence of Organic Solvent
Hahnvajanawong, Viwat,Phungpis, Baramee
, p. 2671 - 2674 (2021/10/25)
N-Aroylbenzotriazoles have been shown to be efficient reagents for esterification in the absence of organic solvent. Grinding of N-aroylbenzoytiazoles with twofold excess of alcohols for a couple of hours at room temperature gave corresponding esters in high percentage of yields.
A metal-free iodine-mediated conversion of hydroxamates to esters
Ghosh, Subhankar,Banerjee, Jeet,Ghosh, Rajat,Chattopadhyay, Shital K.
, p. 1353 - 1360 (2020/03/30)
A metal-, oxidant-, and additive-free conversion of hydroxamates to esters have been achieved using molecular iodine as the reagent using a novel but not-so-explored heron-type rearrangement. The reaction proceeds with almost equal facility with substrates having either electron-donating or electron-withdrawing substituent. Similarly, α,?-unsaturated, and sterically hindered ortho-substituted hydroxamates also undergo the desired transformation smoothly.
Mechanochemical Palladium-Catalyzed Carbonylative Reactions Using Mo(CO)6
van Bonn, Pit,Bolm, Carsten,Hernández, José G.
, p. 2576 - 2580 (2020/02/20)
Esters and amides were mechanochemically prepared by palladium-catalyzed carbonylative reactions of aryl iodides by using molybdenum hexacarbonyl as a convenient solid carbonyl source and avoiding a direct handling of gaseous carbon monoxide. Real-time monitoring of the mechanochemical reaction by in situ pressure sensing revealed that CO is rapidly transferred from Mo(CO)6 to the active catalytic system without significant release of molecular carbon monoxide.
Bu 4 NI-Catalyzed C-C Bond Cleavage and Oxidative Esteri??cation of Allyl Alcohols with Toluene Derivatives
Chen, Yaoyao,Cui, Yongmei,Jia, Xueshun,Li, Chengliang,Li, Jian,Sun, Mingming
, p. 3667 - 3674 (2019/09/30)
A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C-C bond cleavage and C-O bond forming.
Palladium-Catalyzed Carbonylative Synthesis of Benzyl Benzoates Employing Benzyl Formates as Both CO Surrogates and Benzyl Alcohol Sources
Lai, Ming,Qi, Xinxin,Wu, Xiao-Feng
supporting information, p. 3776 - 3778 (2019/06/24)
An efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of benzyl benzoates from aryl bromides has been developed. Benzyl formates have been explored as a new type of efficient and useful CO sources and also reaction partners. A wide range of benzyl benzoates was obtained in good to excellent yields.
Palladium-Catalyzed Alkoxycarbonylation of Arylsulfoniums
Minami, Hiroko,Nogi, Keisuke,Yorimitsu, Hideki
supporting information, p. 2518 - 2522 (2019/04/17)
Alkoxycarbonylation of arylsulfoniums has been developed with the aid of a catalytic amount of a palladium-Xantphos complex under an atmospheric pressure of CO gas. Various functional groups such as carbonyl, cyano, halo, and sulfonyl groups were well tolerated under the present catalysis. Since aryldimethylsulfoniums were readily prepared from the corresponding aryl methyl sulfides and methyl triflate, one-pot alkoxycarbonylation of aryl methyl sulfides could be accomplished.
Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required
Kwon, Young-Do,La, Minh Thanh,Kim, Hee-Kwon
, p. 10833 - 10841 (2018/07/05)
A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.
Versatile Heterogeneous Palladium Catalysts for Diverse Carbonylation Reactions under Atmospheric Carbon Monoxide Pressure
Vico Solano, Marta,González Miera, Greco,Pascanu, Vlad,Inge, A. Ken,Martín-Matute, Belén
, p. 1089 - 1095 (2018/02/06)
Herein, we report a versatile carbonylation protocol using heterogeneous Pd0 nanoparticles supported on the metal–organic frameworks (MOFs) MIL-88B-NH2 (Fe/Cr). The synthesis of a vast array of carbonyls, which includes amides, esters, carboxylic acids, and α-ketoamides, was achieved through mono- and dicarbonylation reactions. The selectivity could be controlled simply by tuning the reaction conditions. Superior activity and selectivity were recorded in some cases compared to that achieved with commercial Pd/C. However, the utility of an elaborate catalyst support is questionable and important reactivity and recyclability issues are discussed.
Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism
Huang, Hai,Kang, Jun Yong
supporting information, p. 544 - 547 (2017/02/10)
An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronucleophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.
