53422-19-8Relevant academic research and scientific papers
N-Methylpyrrolidin-2-one-Promoted Formation of Functional Esters through C–O Bond Cleavage
Liu, Jianming,Wang, Yanyan,Yue, Yuanyuan,Liu, Na,Zhang, Jian,Zhao, Shufang,Tang, Qinghu,Zhuo, Kelei
supporting information, p. 2641 - 2647 (2017/05/19)
Trifluoromethanesulfonic acid catalyzed C–O bond cleavage leading to the preparation of functional esters in the presence of N-methylpyrrolidin-2-one (NMP) was accomplished. Various substrates were well tolerated, and a gram-scale experiment was successfully realized. DFT calculations indicated that NMP plays a decisive role in accelerating nucleophilic attack of the functional acid to generate the functional esters in chlorobenzene.
Expedient carbonylation of aryl halides in aqueous or neat condition
Ang, Wei Jie,Lo, Lee-Chiang,Lam, Yulin
, p. 8545 - 8558 (2014/12/11)
An expedient and versatile, microwave-assisted procedure for the carbonylation of aryl halides with boronic acids, alcohols or amines in water or under neat conditions has been developed. The reaction is catalyzed by fluorous, oxime-based palladacycle 1 that shows an excellent recyclable property and low levels of Pd leaching. To demonstrate the usefulness of the protocol, we applied it to the preparation of compounds of pharmaceutical interest, including a precursor of the reverse transcriptase inhibitor, niacin, benzocaine and butamben.
Transition metal free oxidative esterification of alcohols with toluene
Liu, Lianghui,Yun, Lin,Wang, Zikuan,Fu, Xuefeng,Yan, Chun-Hua
supporting information, p. 5383 - 5386 (2013/09/12)
Using Bu4NI as the catalyst and tert-butyl hydroperoxide as the oxidant, direct esterification of alcohols with toluene derivatives was achieved. Mechanistic investigations indicate that the alcohols are sequentially oxidized to aldehydes, carboxylic acids, and then to benzyl esters. Bu 4N+ functions as a phasetransfer reagent and iodide catalyzes the reaction.
Cooperative N-Heterocyclic Carbene (NHC) and Ruthenium Redox Catalysis: Oxidative Esterification of Aldehydes with Air as the Terminal Oxidant
Zhao, Junfeng,Mueck-Lichtenfeld, Christian,Studer, Armido
supporting information, p. 1098 - 1106 (2013/05/21)
The paper describes a cooperative NHC (N-heterocyclic carbene) and ruthenium-based redox catalysis for the mild aerobic oxidative esterification of various aromatic and heteroaromatic aldehydes. The ruthenium(II) complex Ru(bpz)3(PF6)2 (bpz=2,2′-bipyrazine) as catalyst is shown to be compatible with free NHCs. The NHC is used in these cascade reactions for the umpolung of the aldehyde to form the corresponding Breslow intermediate which in turn gets oxidized to an acylazolium ion by the ruthenium redox catalyst. Air is used as a terminal oxidant for oxidation (regeneration) of the ruthenium catalyst. In addition, we will show that in the absence of the ruthenium redox catalyst and alcohol, NHC-catalyzed aerobic oxidation of aldehydes delivers the corresponding acids in good to excellent yields. Mechanistic studies and DFT calculations supporting our suggested mechanisms are provided. Copyright
Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions
Bhattacharya, Apurba,Patel, Nitin C.,Vasques, Tomas,Tichkule, Ritesh,Parmar, Gaurang,Wu, Jiejun
, p. 565 - 567 (2007/10/03)
A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.
Synthesis of aromatic esters catalyzed by palladium on charcoal: An efficient heterogeneous catalyst for alkoxycarbonylation of aryl iodides
Ramesh, Chinnasamy,Nakamura, Ryo,Kubota, Yoshihiro,Miwa, Minoru,Sugi, Yoshihiro
, p. 501 - 504 (2007/10/03)
Palladium on charcoal was found to catalyze the carbonylation of aryl iodides with various aliphatic alcohols as well as less reactive phenols to give the corresponding esters in high yield at 140°C and in the presence of carbon monoxide (1.0 MPa). The carbonylation-polycondensation of 2,7-diiodo-9,10-dihydrophenanthrene with bisphenol-A afforded high molecular weight polyarylate, poly [oxy-1,4-phenylene (1-methylethylidene)-1,4-phenyleneoxycarbonyl (9,10-dihydro-2,7-phenanthrenediyl) carbonyl].
Mitsunobu reaction modifications allowing product isolation without chromatography: Application to a small parallel library
Pelletier, Jeffrey C.,Kincaid, Scott
, p. 797 - 800 (2007/10/03)
Readily available reagents, triphenylphosphine resin and di-t- butylazodicarboxylate, were used in Mitsunobu reactions and the byproducts were removed without chromatography. The new modification was utilized to prepare a small, parallel, solution phase library. (C) 2000 Elsevier Science Ltd.
