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.
Esterification of the Primary Benzylic C-H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation
Lu, Bing,Zhu, Fan,Sun, Hong-Mei,Shen, Qi
supporting information, p. 1132 - 1135 (2017/03/14)
The first iron-catalyzed esterification of the primary benzylic C-H bonds with carboxylic acids using di-tert-butyl peroxide as an oxidant is achieved by novel ionic iron(III) complexes containing an imidazolinium cation. The use of well-defined, air-stable, and available iron(III) complex in a 5 mol % loading and readily available starting materials with a broad generality and outstanding sterically hindered tolerance renders this methodology a useful alternative to other protocols that are typically employed for the synthesis of benzyl esters.
Palladium-Catalyzed Decarboxylation of Benzyl Fluorobenzoates
Makida, Yusuke,Matsumoto, Yasutaka,Kuwano, Ryoichi
supporting information, p. 2573 - 2576 (2017/10/09)
The decarboxylation of benzyl fluorobenzoates has been developed by using the palladium catalyst prepared in situ from Pd(η 3 -allyl)Cp and bulky monophosphine ligand XPhos. The catalytic reaction afforded a range of fluorinated diarylmethanes in good yields with broad functional-group compatibility. The substrates were readily synthesized by condensation of the corresponding benzoic acid with benzyl alcohol. Therefore, the transformation is formally regarded as a cross-coupling reaction between fluorine-containing benzoic acids and benzyl alcohols.
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.
Polymer-assisted solution-phase library synthesis of 4-alkoxy-2-hydroxy-3,5,6-trifluorobenzoic acids
Hardcastle, Ian R.,Moreno Barber, Amelia,Marriott, Jonathan H.,Jarman, Michael
, p. 1363 - 1365 (2007/10/03)
The efficient synthesis of a small library of 4-alkoxy-2-hydroxy-3,5,6-trifluorobenzoic acids is described via the fluoride mediated alkylation of 5,6,8-trifluoro-7-hydroxy-2-methyl-benzo[1,3]dioxin-4-one with a collection of structurally diverse bromoalkanes. The use of ion-exchange resins during the reaction sequence enabled the preparation of the majority of the products in 82-98% purity without the need for chromatography.
