102970-80-9Relevant articles and documents
Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
Fang, Jing,Li, Ting,Ma, Xiang,Sun, Jiuchang,Cai, Lei,Chen, Qi,Liao, Zhiwen,Meng, Lingkui,Zeng, Jing,Wan, Qian
supporting information, p. 288 - 292 (2021/07/25)
A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.
Silver-catalyzed one-pot synthesis of benzyl 2-alkynoates under ambient pressure of CO2and ligand-free conditions
Guo, Fang-Jie,Zhang, Zhi-Zhi,Wang, Jing-Yun,Sun, Jing,Fang, Xiang-Chen,Zhou, Ming-Dong
, p. 900 - 906 (2017/01/28)
The carboxylative coupling of aryl/alkyl terminal alkynes, CO2and benzyl halides was investigated using silver iodide as the catalyst and Cs2CO3as the base in CH3CN under ligand-free conditions. This reaction protocol shows a wide substrate scope and high functional group tolerance ability for benzyl halides, in which various functionalized benzyl 2-alkynoates were achieved in good yields. This one-pot, ligand-free and CH3CN mediated reaction proved to be easy to handle and could be facilitated under atmospheric CO2pressure.
Spontaneous formation of PMB esters using 4-methoxybenzyl-2,2,2- trichloroacetimidate
Shah, Jigisha P.,Russo, Christopher M.,Howard, Kyle T.,Chisholm, John D.
supporting information, p. 1740 - 1742 (2014/03/21)
Carboxylic acids are converted to the corresponding 4-methoxybenzyl (PMB) esters with 4-methoxybenzyl-2,2,2-trichloroacetimidate in the absence of an acid catalyst. This operationally simple procedure is a highly effective method for the formation of PMB esters. The reaction is promoted by the carboxylic acids themselves in excellent yields (72-99%). Sterically hindered carboxylic acids, which provide lower yields with other imidates, are esterified in higher yield with the more reactive PMB imidate. No racemization is observed in the case of carboxylic acids bearing an α-stereocenter, and no isomerization is observed with Z-α,β-unsaturated acids. This method may therefore find use in the esterification of complex or sensitive substrates where more common techniques lead to decomposition.
