- In situ activation of benzyl alcohols with XtalFluor-E: Formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation
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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
- Desroches, Justine,Champagne, Pier Alexandre,Benhassine, Yasmine,Paquin, Jean-Franois
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supporting information
p. 2243 - 2246
(2015/03/04)
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- Benzylation of arenes with benzyl halides synergistically promoted by in situ generated superacid boron trifluoride monohydrate and tetrahaloboric acid
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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.
- Huang, Ruofeng,Zhang, Xiaohui,Pan, Jing,Li, Jiaqiang,Shen, Hang,Ling, Xuege,Xiong, Yan
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supporting information
p. 1540 - 1546
(2015/03/04)
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- An improved method for the synthesis of triarylmethanes using heterogenized 12-tungestocobaltic acid
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Two heterogeneous catalysts based on 12-tungestocobaltic acid, including K5CoW12O40 and H5CoW 12O40 supported on rice husk ash extracted nano silica (CoW/NSiO2), were used in sel
- Rafiee, Ezzat,Jalilian, Fereshteh
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p. 203 - 207
(2014/05/20)
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- Superacid BF3-H2O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water
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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.
- Zhang, Shuting,Zhang, Xiaohui,Ling, Xuege,He, Chao,Huang, Ruofeng,Pan, Jing,Li, Jiaqiang,Xiong, Yan
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p. 30768 - 30774
(2014/08/05)
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- Benzylation of arenes with benzyl ethers promoted by the in situ prepared superacid BF3-H2O
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An efficient and environmentally friendly benzylation of arenes with benzyl ethers as benzyl donors using BF3-Et2O to generate in situ the superacid BF3-H2O as an efficient promotor has been described. A wide variety of functional groups have been investigated and found to be compatible to give the desired diarylmethanes in yields of up to 99%. The crucial role of the moisture content in this transformation has been demonstrated by detailed investigations. This journal is the Partner Organisations 2014.
- Li, Yu,Xiong, Yan,Li, Xueming,Ling, Xuege,Huang, Ruofeng,Zhang, Xiaohui,Yang, Jianchun
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p. 2976 - 2981
(2014/06/10)
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- Direct alkylation of aromatics using alcohols in the presence of NaHSO 4/SiO2
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Simple and efficient procedure for alkylation of aromatics from alcohols in the presence of NaHSO4/SiO2 was developed. Various triaryl methanes were obtained in good yields in short reaction time. For instance the reaction of mesitylene with benzhydrol in the presence of NaHSO4/SiO2 gave the corresponding triaryl methane in a quantitative yield. NaHSO4/SiO2 was regenerated by simple treatment and could be recycled eight times without activity loss.
- Sato, Yuta,Aoyama, Tadashi,Takido, Toshio,Kodomari, Mitsuo
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supporting information; experimental part
p. 7077 - 7081
(2012/08/28)
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- Iron(iii)-based ionic liquid-catalyzed regioselective benzylation of arenes and heteroarenes
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An easily prepared Fe(iii)-derived Lewis acid ionic liquid ([C 4mim][FeCl4]), being comprised of 1-butyl-3-methyl imidazolium cation and tetrachloroferrate anion, was found to be an efficient, recyclable catalyst for benzylation of various arenes/heteroarenes into the diarylmethanes derivatives under mild reaction conditions without utilization of additional organic solvent. Interestingly, the acidity of [C 4mim][FeCl4] could account for its catalytic activity in promoting the Lewis acid-catalyzed alkylation. Notably, this type of Fe(iii)-based ionic liquid (IL) shows excellent stability, and could be easily recovered, and reused for five times without significant loss of its catalytic activity.
- Gao, Jian,Wang, Jin-Quan,Song, Qing-Wen,He, Liang-Nian
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supporting information; experimental part
p. 1182 - 1186
(2011/06/25)
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- Highly efficient method for solvent-free synthesis of diarylmethane and triarylmethane from benzylic alcohols using P2O5/Al 2O3 or P2O5/SiO2 at room temperature
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A highly efficient procedure for the synthesis of triarylmethane and diarylmethane via benzylation of aromatic hydrocarbons from benzyl alcohols using supported P2O5 on SiO2 and/or Al 2O3 under solvent-free conditions is described. Excellent yields of triarylmethane and diarylmethane were obtained using P 2O5-SiO2 (50%W/W) and/or P2O 5-Al2O3 (50%W/W) at room temperature. The reusability of both supported P2O5 on SiO2 and Al2O3 were examined. Both supported reagents show favorable activities in first and second runs, however, a decline in reactivity was observed in following attempts. The reaction is scalable to > 0.03 mole amounts.
- Khazaei, Ardeshir,Rad, Mohammad Navid Soltani,Borazjani, Maryam Kiani,Moradian, Khadijeh Mansouri,Borazjani, Mohammad Kiani,Zebarjadian, Mohammad Hassan
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experimental part
p. 120 - 126
(2012/06/18)
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- An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates
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(Chemical Equation Presented) Green grow the diarylmethanes: Substituted arenes and heteroarenes can be easily benzylated in the presence of inexpensive and relatively nontoxic metal salts such as FeCl3 (see scheme). This arylation method with benzyl alcohols is a state-of-the-art green route to diarylmethanes as water is the only by-product.
- Iovel, Irina,Mertins, Kristin,Kischel, Jette,Zapf, Alexander,Beller, Matthias
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p. 3913 - 3917
(2007/10/03)
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