Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B 12 Model Complex under Aerobic Conditions

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Abstract

A visible light responsive catalytic system with the B 12 complex as the catalyst and [Ir(dtbbpy)(ppy) 2 ]PF 6 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.

Original languageEnglish
Pages (from-to)237-240
Number of pages4
JournalChemPlusChem
Volume84
Issue number3
DOIs
Publication statusPublished - Mar 1 2019

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Amides
Amines
Organic compounds
Photosensitizing Agents
Precious metals
Gases
Catalysts
Temperature

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B 12 Model Complex under Aerobic Conditions",
abstract = "A visible light responsive catalytic system with the B 12 complex as the catalyst and [Ir(dtbbpy)(ppy) 2 ]PF 6 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.",
author = "Hui Tian and Hisashi Shimakoshi and Toshikazu Ono and Yoshio Hisaeda",
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AU - Tian, Hui

AU - Shimakoshi, Hisashi

AU - Ono, Toshikazu

AU - Hisaeda, Yoshio

PY - 2019/3/1

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N2 - A visible light responsive catalytic system with the B 12 complex as the catalyst and [Ir(dtbbpy)(ppy) 2 ]PF 6 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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