1233342-41-0

Upstream product

• 151-10-0 1,3-Dimethoxybenzene 
• 98-83-9 isopropenylbenzene 
• 14629-57-3 1-phenyl-1-methyl-1-trimethylsiloxyethane 
• 617-94-7 1-methyl-1-phenylethyl alcohol 

Relevant academic research and scientific papers

Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility

Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity. The protocol is characterized by a wide substrate scope and excellent functional group tolerance. Notably, this process constitutes the first general application of graphenes to promote direct C-C bond formation utilizing polar functional groups anchored on the GO surface, thus opening the door for an array of functional group alkylations using benign and readily available graphene materials. Mechanistic studies suggest that the reaction proceeds via a tandem catalysis mechanism in which both of the coupling partners are activated by interaction with the GO surface.

Iron-catalyzed friedel-crafts benzylation with benzyl TMS ethers at room temperature

Friedel-Crafts benzylations between unactivated arenes and benzyl alcohol derivatives are clean and straightforward processes to construct biologically useful di- and triarylmethanes. We have established an efficient iron-catalyzed Friedel-Crafts benzylation method at room temperature that uses benzyl TMS ethers as substrates, which are poorly reactive under common nucleophilic substitution conditions. The reaction seems to progress through iron-catalyzed self-condensation of the benzyl TMS ether to the corresponding dibenzylic ether. The use of excess arene relative to benzyl TMS ether produced mono-benzylated arene (diand tri-arylmethane products), whereas the use of excess benzyl TMS ether versus arene provided bis-benzylated arene (polyarylated products) in high yields and regioselectivities. In previous methods, the latter double Friedel-Crafts benzylations hardly proceed.

Calcium-catalyzed hydroarylation of alkenes at room temperature

Calcium-catalyst gaining ground: A variety of electron-poor electron-rich and trisubstituted styrene derivatives were reacted to give the desired diarylalkanes within less than an hour at room temperature in the presence of 2.5 mol % of Ca(NTf2)2/Bu4NPF6 (see scheme). Additionally the highly reactive calcium catalyst was successfully applied for the hydroarylation of dienes and even trisubstituted olefins.

Calcium-catalyzed friedel-crafts alkylation at room temperature

Chemical Equatation Representation A novel calcium catalyst was found to efficiently functionalize electron-rich arenes with secondary and tertiary benzylic, propargylic, and allylic alcohols under very mild reaction conditions. The new catalyst system significantly enlarges the scope of the reaction, which was previously limited except for the few examples with secondary benzylic alcohols.