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Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

Xiao Cheng, Bao-Gui Cai, Hui Mao, Juan Lu, Lei Li, Kun Wang* and Jun Xuan*

*College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, People's Republic of China, Email: wangkunahu.edu.cn, xuanjunahu.edu.cn

X. Cheng, B.-G. Cai, H. Mao, J. Lu, L. Li, K. Wang, J. Xuan, Org. Lett., 2021, 23, 4109-4114.

DOI: 10.1021/acs.orglett.1c00979 (free Supporting Information)


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Abstract

A visible light-promoted divergent cycloaddition of α-diazo esters to hexahydro-1,3,5-triazines provides a series of aziridines and imidazolidines in good yield, by simply changing the reaction media. The reactions occur under visible light irradiation without photoredox catalysts.

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General procedure for the Synthesis of Aziridines

To a 10 mL Schlenk flask equipped with a magnetic stir bar was added α-diazo ester (0.45 mmol), triazine (0.05 mmol), dry DMSO (2.0 mL). The resulting mixture was degassed via 'freeze-pump-thaw' procedure (3 times). Right after, the solution was stirred at ~3 cm from a 24 W blue LED at room temperature for 12 h. The solvent was removed by vacuum and the crude product was purified by flash chromatography on silica gel to provide pure product. Size: 200~300 mesh; eluent: petroleum ether/ethyl acetate (20:1~5:1).

General procedure for the Synthesis of Imidazolidines

To a 10 mL Schlenk flask equipped with a magnetic stir bar was added  α-diazo ester (0.2 mmol), triazine (0.1 mmol), dry DCM (2.0 mL). The resulting mixture was degassed via 'freeze-pump-thaw' procedure (3 times). Right after, the solution was stirred at a distance of ~3 cm from a 24 W blue LED at room temperature for 12 h. The solvent was removed by vacuum and the crude product was purified by flash chromatography on silica gel to provide pure product. Size: 200~300 mesh; eluent: petroleum ether/ethyl acetate (20:1~5:1).


Key Words

aziridines, imidazolidines, photochemistry


ID: J54-Y2021