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Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B12 Model Complex under Aerobic Conditions
Hui Tian1, Hisashi Shimakoshi1, Toshikazu Ono1
1Department of Chemistry and Biochemistry Graduate School of Engineering, Kyushu University 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.
Abstract:
A visible light responsive catalytic system with the B12 complex as the catalyst and [Ir(dtbbpy)(ppy)2 ]PF6 as the photosensitizer was developed. It provides a convenient and efficient way to synthesize amides. Based on this method, trichlorinated organic compounds were converted into amides in the presence of an amine under aerobic conditions at room temperature in a one-pot procedure. Various trichlorinated organic compounds and an amine source, such as primary, secondary, and cyclic amines, have been evaluated for this transformation, providing the expected products in moderate to excellent yields. Notably, product formation depended on the reaction atmosphere where the amide was obtained under aerobic conditions while partially dechlorinated products were obtained under anaerobic conditions. As this protocol is free from hazardous reagents, extra additives, noble metals, and dangerous gas, the present method provides a novel and efficient approach for amide synthesis under mild and easily controlled conditions.
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