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제117회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Pd- and Cu-catalyzed Syntheses of Multifunctionalized Fused N-Heterocycles

2016년 2월 18일 17시 28분 55초
ORGN3-3 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
금 15시 : 30분
유기화학 - 유기화학의 최신 동향 III: 촉매와 유기합성 (Current Trends in Organic Chemistry III: Catalysis and Synthesis)
저자 및
부산대학교 화학과, Korea
Nitrogen-containing fused N-heterocycles are key components of a wide variety of important synthetic pharmaceuticals, agrochemicals, biochemical fluorescent probes, and electronic materials. Consequently, a significant level of interest exists in developing efficient methods for the synthesis of substituted derivatives of these N-heterocycles. In the first part of presentation, a direct method for arylation of 1,2-azolo[1,5-a]pyridines will be discussed. The fused pyridines react with aryl halides in the presence of Pd(OAc)2(Phen) as a catalyst and CuCl as a Lewis acid to form arylated derivatives. While pyrazolo[1,5-a]pyridines and [1,2,4]triazolo[1,5-a]pyridines are arylated at ortho-positions of their pyridine rings using this method, in situ ring-opening of the formed C-7 arylated [1,5-a] pyridine takes place to generate 2,6-disubstituted pyridine. Also, upon treatment with LDA, C-7 arylated pyrazolo[1,5-a]pyridine-3-carboxylate reacts to produce diversely substituted 2,6-disubstituted pyridines. In the second part, a Cu(I)-catalyzed tandem cyclization/alkynylation of propargylic amines will be presented. This synthetic method provides rapid access to functionalized pyrrolo-fused heterocycle derivatives under mild reaction conditions. The reaction first proceeded via a 5-endo-dig aminocupration, followed by a coupling between the copper-bound intermediate and alkynyl bromide, to afford the products in good to excellent yields. Some of fused N-heterocycles were utilized as backbone of abnormal NHC ligands for Rh, Ag, Au, and Pd. We demonstrated these abnormal NHC ligands showed rate-acceleration effect on Suzuki-Miyaura reaction. More details will be provided in the presentation.