Burapha University International Conference, BUU-2014

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Synthesis of unsymmetrical triarylmethanes via Friedel-Crafts reaction of N-Boc or N-CBz diarylmethylcarbamates
Sureeporn Ruengsangtongkul, Soroat Kankasikam, Nareenart Yensabai, ๋Jaray Jaratjaroonphong

Last modified: 2014-05-27

Abstract


In this research, we have developed an efficient synthesis of unsymmetrical triarylmethanes via a novel Friedel-Crafts reaction of electron-rich arenes using N-Boc or N-benzyl-diarylmethylcarbamates as alkylating agent. The N-Boc or N-benzyl-diarylmethylcarbamates were prepared smoothly from our methodology via one-pot, three component reaction of electron-rich arenes, aromatic aldehydes and N-Boc or N-benzylcarbamates in the presence of 5 mol% of FeCl3·6H2O in toluene at room temperature. The N-Boc or N-benzyl-diarylmethylcarbamates were then reacted with electron-rich arenes in CH2Cl2 at room temperature employing I2 (10 mol%) as catalyst to afford unsymmetrical triarylmethanes in 14-93% yields. The use of mild reaction condition, commercially available as well as inexpensive catalyst, low catalyst loading, and environmentally catalyst are advantages of the present method.

 


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