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Visible-Light-Induced Imide Synthesis through a Nitrile Ylide Formation/Trapping Cascade

Bao-Gui Cai, Wei-Zhong Yao, Lei Li and Jun Xuan*

*College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601, People’s Republic of China, Email:

B.-G. Cai, W.-Z. Yao, L. Li, J. Xuan, Org. Lett., 2022, 24, 6647-6652.

DOI: 10.1021/acs.orglett.2c02671

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A visible-light-promoted three component reaction of diazo compounds, nitriles, and carboxylic acids provides a wide range of imide products in very good yield. The reaction utilizes acceptor-only diazo compounds as carbene precursors and nitriles as carbene-trapping reagents to form the key nitrile ylides.

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proposed mechanism

General procedure

To a 10 mL Schlenk flask equipped with a magnetic stir bar was added ethyl diazoacetate (45.6 mg, 0.40 mmol, 4.0 equiv.), benzoic acid (12.2 mg, 0.10 mmol, 1.0 equiv.), dry MeCN (1.0 mL). The resulting mixture 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 silica: 200~300; eluant: petroleum ether/ethyl acetate (10:1) to provide pure product.

Key Words

imides, photochemistry, multicomponent reactions

ID: J54-Y2022