500362-29-8Relevant articles and documents
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Kundinger,Ovist
, p. 2501 (1954)
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In situ activation of benzyl alcohols with XtalFluor-E: Formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation
Desroches, Justine,Champagne, Pier Alexandre,Benhassine, Yasmine,Paquin, Jean-Franois
supporting information, p. 2243 - 2246 (2015/03/04)
The Friedel-Crafts benzylation of arenes using benzyl alcohols activated in situ with XtalFluor-E is described. A wide range of 1,1-diarylmethanes and 1,1,1-triarylmethanes were prepared under experimentally simple and mild conditions, without the need for a transition metal or a strong Lewis acid. Notably, the reactivity observed demonstrates the potential of XtalFluor-E to induce C-OH bond ionization and SN1 reactivity of benzylic alcohols. This journal is
Superacid BF3-H2O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water
Zhang, Shuting,Zhang, Xiaohui,Ling, Xuege,He, Chao,Huang, Ruofeng,Pan, Jing,Li, Jiaqiang,Xiong, Yan
, p. 30768 - 30774 (2014/08/05)
A convenient procedure employing simple starting materials benzyl alcohols and acetates as the benzyl donors to assemble a series of diarylalkanes through benzylation of arenes using in situ prepared superacid BF3-H 2O as an efficient promoter has been developed. The beneficial role of water in the reaction has been clarified with combination of control experiments and 11B NMR analysis. This reaction is a self-promoted model, which is triggered by the trace of water and continuously promoted by self released by-product water (or carboxylic acid). A wide range of substrates are investigated and the moderate to excellent yields and the good regioselectivities for secondary benzyl alcohols as well as arenes bearing electron-withdrawing groups have been achieved. As a result, moisture in the reaction system has been utilized as an efficient initiator in all benzylation cases.