TY - JOUR
T1 - Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B 12 Model Complex under Aerobic Conditions
AU - Tian, Hui
AU - Shimakoshi, Hisashi
AU - Ono, Toshikazu
AU - Hisaeda, Yoshio
N1 - Funding Information:
This study was partially supported by JSPS KAKENHI Grant Numbers 18H04265 in Precisely Designed Catalysts with Customized Scaffolding and Grant Number JP16H04119, and by JSPS and PAN under the Research Cooperative Program Grant Number AJ180081 (30-0004-04) and a Grant from the Nippon Sheet Glass Foundation (HAKF541800).
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/3
Y1 - 2019/3
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.
AB - 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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U2 - 10.1002/cplu.201800522
DO - 10.1002/cplu.201800522
M3 - Article
C2 - 31950763
AN - SCOPUS:85058041006
SN - 2192-6506
VL - 84
SP - 237
EP - 240
JO - ChemPlusChem
JF - ChemPlusChem
IS - 3
ER -