102002-13-1Relevant academic research and scientific papers
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.
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.
