reduction of nitroarenes to azoxybenzenes by potassium borohydride in water减少nitroarenes硼氢化钾氧化偶氮苯的水.pdfVIP

Molecules 2011, 16, 3563-3568; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water Yufang Liu 1, Bo Liu 2,*, Ailing Guo 1, Zhenming Dong 1, Shuo Jin 1 and Yun Lu 3 1 School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China 2 School of Science, Beijing Jiaotong University, Beijing 100044, China 3 Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL 62026, USA * Author to whom correspondence should be addressed; E-Mail: boliu413@; Tel.: +86-10 Fax: +86-10 Received: 24 February 2011; in revised form: 15 April 2011 / Accepted: 22 April 2011 / Published: 28 April 2011 Abstract: The synthesis of the azoxybenzenes by the reduction of nitroarenes with reducing agent potassium borohydride in water was reported for the first time. PEG-400 was used as a phase transfer catalyst and could effectively catalyze the reduction. The electronic effects of substituent groups play an important role in determining the reduction efficiencies. Electron-withdrawing substituents promote the formation of the azoxybenzene products, while electron-releasing groups retard the reductions to various degrees depending on the extent of their electron-donating ability. Keywords: nitroarenes; azoxybenzenes; potassium borohydride; water; PEG-400 1. Introduction In 1956, Weill and Panson obtai