7249-83-4Relevant articles and documents
Two-component boronic acid catalysis for increased reactivity in challenging Friedel-Crafts alkylations with deactivated benzylic alcohols
Ang, Hwee Ting,Rygus, Jason P. G.,Hall, Dennis G.
, p. 6007 - 6014 (2019/06/24)
A general and efficient boronic acid catalyzed Friedel-Crafts alkylation of arenes with benzylic alcohols was previously developed for the construction of unsymmetrical diarylmethane products (X. Mo, J. Yakiwchuk, J. Dansereau, J. A. McCubbin and D. G. Hall, J. Am. Chem. Soc., 2015, 137, 9694). Highly electron-deficient benzylic alcohols, however, were ineffective coupling partners due to the increased difficulty of C-O bond ionization. Herein, we report the use of perfluoropinacol as an effective co-catalyst to improve the reactivity of a boronic acid catalyst in the Friedel-Crafts benzylations of electronically deactivated primary and secondary benzylic alcohols. According to spectroscopic studies, it is believed that perfluoropinacol condenses with the arylboronic acid catalyst to form a highly electrophilic and Lewis acidic boronic ester. This in situ formed species enables a more facile ionization of the benzylic alcohols likely through a mode of activation promoted by a Lewis acid assisted hydronium Br?nsted acid generated from the interactions of the transient boronic ester with hexafluoroisopropanol solvent and water.
SO3H-functionalized organic-inorganic ionic liquids based on polyoxometalates characterization and their application in C-C coupling reaction
Rafiee, Ezzat,Mirnezami, Fakhrosadat,Kahrizi, Masoud
, p. 332 - 339 (2016/05/19)
Different ionic liquids (ILs) with SO3H as functional group were achieved by combining SO3H-functionalized organic cations and polyoxometalates (POM). The obtained salts were characterized and their catalytic activities investigated
Benzylation of arenes with benzyl halides synergistically promoted by in situ generated superacid boron trifluoride monohydrate and tetrahaloboric acid
Huang, Ruofeng,Zhang, Xiaohui,Pan, Jing,Li, Jiaqiang,Shen, Hang,Ling, Xuege,Xiong, Yan
supporting information, p. 1540 - 1546 (2015/03/04)
To examine the assembly methodology of diarylmethanes, a benzylation of (hetero)arenes with benzyl halides has been developed and various diarylmethanes were furnished with yields of up to 98% and regioselectivities of up to >99%. The complexation of the by-product halogen hydride with BF3·OEt2 generated the Bronsted acid BF3·HX (HBF3X, X=Cl or Br) in situ to synergistically promote the benzylation.