Abstract
Chemical synthesis of organic compounds is often a complex process that requires toxic catalysts, long reaction times, and many reagents. One example is the conventional synthesis of 2,1-benzisoxazole (BNZ). This compound has great importance for both pharmaceutical applications and as a starting material in the total synthesis of natural products.1 Chemical synthesis of this compound requires use of ruthenium and palladium catalysts, high pressure of carbon monoxide, and long reaction times.2 Also, the yield for the conventional chemical reaction is low, and there are no reports of yields higher than 50%.3 On the other hand, electrochemistry offers a clean and fast method for the synthesis of organic compounds. However, the electrosynthesis of BNZ has previously involved the use of a mercury pool cathode over a long reaction time, which makes the synthesis unfavorable.4 In the present work, the electrochemical behavior of o-nitrobenzaldehyde was studied in different solvent systems with the aid of cyclic voltammetry. Subsequently, the electrosynthesis of BNZ was accomplished with bulk electrolysis at a carbon cathode. Upon optimization, the yield of the BNZ reached 80% within a 1-hour electrolysis without any catalyst to facilitate the process. References Wiȩcław, M.; Bobin, M.; Kwast, A.; Bujok, R.; Wróbel, Z.; Wojciechowski, K. Mol. Divers. 2015, 19, 807–816.Akazome, M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1994, 59, 3375–3380.Genung, N. E.; Wei, L.; Aspnes, G. E. R. Org. Lett. 2014, 16, 3114–3117.Fijalek, Z.; Zuman, P. Electroanal. 1993, 5, 53–64. Figure 1
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