66310-15-4Relevant articles and documents
Metal-free transesterification catalyzed by tetramethylammonium methyl carbonate
Hatano, Manabu,Tabata, Yuji,Yoshida, Yurika,Toh, Kohei,Yamashita, Kenji,Ogura, Yoshihiro,Ishihara, Kazuaki
supporting information, p. 1193 - 1198 (2018/03/27)
Environmentally benign metal-free tetramethylammonium methyl carbonate is effective as a catalyst for the chemoselective, scalable, and reusable transesterification of various esters and alcohols in common organic solvents. In situ-generated highly active species, tetramethylammonium alkoxides, can greatly avoid self-decomposition at ≤110 °C, and are reusable. In particular, chelating substrates, such as amino alcohols, diols, triols, sugar derivatives, alkaloids, α-amino acid esters, etc., which deactivate conventional metal salt catalysts, can be used. A 100 gram scale biodiesel production was also demonstrated.
Synthesis of 2-Pyridinemethyl Ester Derivatives from Aldehydes and 2-Alkylheterocycle N-Oxides via Copper-Catalyzed Tandem Oxidative Coupling-Rearrangement
Wang, Chang-Sheng,Roisnel, Thierry,Dixneuf, Pierre H.,Soulé, Jean-Fran?ois
supporting information, p. 6720 - 6723 (2017/12/26)
Successful benzylic C(sp3)-H acyloxylation of 2-alkylpyridine, 2-alkylpyrazine, and 2-alkylthiazole compounds was achieved using simple aldehydes. This was carried out via a copper-catalyzed tandem reaction, involving oxidative esterification followed by O-atom transfer of the resultant high yield formed Boekelheide intermediate. The method enables the preparation of functional heterocycles and the desymmetrization of 2,6-dialkylpyridines for efficient synthesis of dissymmetric pincer ligands, thus offering a new life for more practical Boekelheide rearrangement.
Base-catalyzed retro-Claisen condensation: A convenient esterification of alcohols via C-C bond cleavage of ketones to afford acylating sources
Xie, Feng,Yan, Fengxia,Chen, Mengmeng,Zhang, Min
, p. 29502 - 29508 (2014/08/05)
The base-catalyzed esterification of alcohols via retro-Claisen condensation has been demonstrated for the first time. A variety of alcohols including aryl- and heteroaryl methanols as well as aliphatic ones underwent efficient acylation to give the ester products in reasonable to good yields upon isolation. Not only conventional 1,3-diketones but also strong electron-withdrawing group containing acetophenones could serve as the acylating suppliers. The synthetic protocol is operationally simple and adaptable to a broad substrate scope. It complements the existed esterification via the retro-Claisen condensation, and enlarges this benign synthetic methodology.