75679-47-9Relevant articles and documents
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.
Methyl salicylate as a selective methylation agent for the esterification of carboxylic acids
Chen, Si,Jia, Lei,Li, Xiaonan,Luo, Meiming
, p. 263 - 268 (2014/03/21)
Methyl salicylate is a selective and inexpensive methylating agent for the esterification of carboxylic acids with a wide range of functional group tolerance. The intramolecular hydrogen bonds between the carboxylate and hydroxyl groups in methyl salicylate are essential for the transformation. Allyl, benzyl, methallyl, and propargyl salicylates can also be used as alkylating agents for the preparation of the corresponding alkyl carboxylates.
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