104856-46-4Relevant articles and documents
Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile
Tsuji, Hiroaki,Hashimoto, Keisuke,Kawatsura, Motoi
supporting information, p. 8837 - 8841 (2019/11/11)
The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-pentafluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the ??1- A nd ??3-benzylnickel intermediates.
Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions
Mou, Fen,Sun, Yadong,Jin, Weiwei,Zhang, Yonghong,Wang, Bin,Liu, Zhiqing,Guo, Lei,Huang, Jianbin,Liu, Chenjiang
, p. 23041 - 23045 (2017/07/10)
A metal-free protocol for the direct oxidative esterification of the Csp3-H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.
Fluorous biphasic esterification directed towards ultimate atom efficiency
Xiang, Jiannan,Orita, Akihiro,Otera, Junzo
, p. 4117 - 4119 (2007/10/03)
Aperfectly selective esterification that discriminates between primary and sterically hindered or aromatic carboxylic acids occurs in the presence of the fluoroalkyldistannoxane [{Cl(C6F13CH2 CH2)2SnOSn(CH2CH2 -C6F13)2Cl}2] (1). The reaction gives 100% yield with a strict 1:1 ratio of the carboxylic acid and alcohol reactants, and the catalyst can be recycled without any loss of activity.
