53218-06-7Relevant academic research and scientific papers
Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols
Chu, Xue-Qiang,Ge, Danhua,Luo, Xin-Long,Xu, Pei,Yu, Zi-Lun
supporting information, p. 30937 - 30942 (2021/11/19)
A straightforward aerobic oxidative esterification of aryl aldehydes with alcohols has been developed for the synthesis of substituted esters by employing vitamin B1 as a cost-effective, metal-free, and eco-friendly NHC catalyst. Air is used as a green terminal oxidant. The reaction is a useful addition to the existing NHC-catalytic oxidative esterification.
Dimethylbut-2-ynedioate mediated esterification of acids via sp3 C-N bond cleavage of benzylic tertiary amines
Shen, Hao,Lu, Xing,Jiang, Ke-Zhi,Yang, Ke-Fang,Lu, Yixin,Zheng, Zhan-Jiang,Lai, Guo-Qiao,Xu, Li-Wen
supporting information, p. 8916 - 8923 (2012/10/29)
A straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acids was demonstrated in this manuscript. The present protocol can be regarded as a straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acid. Moreover, the reaction is fundamentally new chemistry for the sp 3 C-N bond cleavage coupled with esterification. The esterification reaction conditions are very mild and functional group-tolerated, such as hydrosilanes, alcohols, phenol, and amino acids. A mechanism is proposed in which the tertiary amine reacts with dimethyl but-2-ynedioate to form zwitterionic salt, and then the zwitterionic intermediate subsequently accept hydrogen to assist the nucleophilic attack of oxygen atom of carboxyl group at the benzyl group of tertiary amine, while a separate reaction pathway leads to esterification.
Monomer-on-monomer (MoM) Mitsunobu reaction: Facile purification utilizing surface-initiated sequestration
Maity, Pradip K.,Rolfe, Alan,Samarakoon, Thiwanka B.,Faisal, Saqib,Kurtz, Ryan D.,Long, Toby R.,Schaetz, Alexander,Flynn, Daniel L.,Grass, Robert N.,Stark, Wendelin J.,Reiser, Oliver,Hanson, Paul R.
supporting information; experimental part, p. 8 - 10 (2011/02/27)
A monomer-on-monomer (MoM) Mitsunobu reaction utilizing norbornenyl-tagged (Nb-tagged) reagents is reported, whereby purification was rapidly achieved by employing ring-opening metathesis polymerization, which was initiated by any of three methods utilizi
Organocatalytic mitsunobu reactions with 3,5-dinitrobenzoic acid
But, Tracy Yuen Sze,Lu, Jinni,Toy, Patrick H.
supporting information; experimental part, p. 1115 - 1117 (2010/06/19)
A second generation procedure for organocatalytic Mitsunobu reactions using 3,5-dinitrobenzoic acid as the pro-nucleophile has been developed. The increased acidity of this acid compared to 4-nitrobenzoic acid, which was used in the original procedure, allowed for higher isolated yields of the desired products and eliminated formation of undesired acetate byproducts. Georg Thieme Verlag Stuttgart - New York.
Organocatalytic Mitsunobu reactions
But, Tracy Yuen Sze,Toy, Patrick H.
, p. 9636 - 9637 (2007/10/03)
A catalytic Mitsunobu reaction system is described in which the azo reagent is used as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant. In this system, iodosobenzene diacetate oxidizes the formed hydrazine byproduct to regenerate the azo reagent. Yields obtained in the catalytic reactions using a variety of carboxylic acids and alcohols were slightly lower than those obtained from corresponding stoichiometric reactions. Both primary and secondary alcohols can be used as substrates in this reaction system, with the secondary alcohols affording products with inverted stereochemistry at the carbinol center. Copyright
