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제125회 대한화학회 학술발표회 및 총회 Photocatalytic Intramolecular C-H Bond Amination Using Plasmonic Au and Au@Pd Core-Shell Nanoparticles

2020년 2월 6일 16시 59분 35초
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Material Chemistry
저자 및
Hyeonji Kim, Youngsoo Kim*
Department of Chemistry, Yeungnam University, Korea
Numerous biologically active natural products and materials have a C-N bond, which is one of the most abundant bonds in organic and medicinal chemistry. Carbazoles are important nitrogen-containing heterocyclic compounds found in the natural products, pharmaceuticals and electronic materials due to their bioactivities and photoconductive properties. Recently, numerous synthetic protocols have been developed to functionalize Carbazole derivatives using transition metals and organic solvent. However, most organic synthetic protocols like Carbazole synthesis have inherent limitations associated with the use of hazardous solvent, high temperature and longer reaction time. Alternatively, photocatalysis with plasmonic noble metal nanoparticles can be a new way to drive organic synthesis with "Green Chemistry" that eliminates the inherent limitations in traditional organic synthesis. In this study, we demonstrated the intramolecular C-H amination of N-benzenesulfonyl amidobiphenyl using plasmonic Au and Au@Pd core-shell nanoparticles under visible light and mild reaction conditions. The products were characterized using spectroscopic analysis, NMR, FT-IR, and GC-MS. Through the NMR and GC-MS analysis, we found the C-H amination was formed, and the N-S bond cleavage in N-benzensulfonyl amidobiphenyl was found. Consequently, we realized that the 9H-Carbazole was synthesized in the presence of Au nanoparticle and visible light. We expect that the photocatalysis technique using plasmonic nanoparticles may apply to diverse types of organic synthesis.