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제122회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Inventing Reactions - Catalytic activation of C-C, C-O, C-N, and C-H bonds

2018년 9월 1일 06시 09분 36초
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목 16시 : 10분
Organic Chemistry - [KCS-GDCh Joint Symposium] Current Trends in Organic Chemistry I: Total Synthesis and Synthetic Methods Development
저자 및
Lukas Gooßen
Chemistry and Biochemistry, Ruhr-Universität Bochum, Germany
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승인 1건

Since our initial report in 2006, decarboxylative coupling reactions, i.e. reactions in which C–C bonds to carboxylate groups are cleaved with formation of new carbon–carbon bonds, have evolved into a powerful synthetic strategy. Their key benefit is that they draw on easily available carboxylic acids rather than expensive organometallic reagents as sources of carbon nucleophiles. Decarboxylative couplings have been utilized e.g. in syntheses of biaryls, vinyl arenes, aryl ketones and aryl ethers. The decarboxylative Chan-Evans-Lam alkoxylation of benzoic acids demonstrates that this reaction concept is applicable also to C–heteroatom bond-forming reactions. In recent variations of this reaction type, the carboxylate groups are first utilized as directing groups for ortho-C–H functionalizations and then either cleaved tracelessly or used as leaving groups in subsequent ipso-substitution reactions. In such transformations, the arene substitution pattern of the benzoate substrates is altered in a defined way, so that they ideally complement the preceding protocols. Besides decarboxylative couplings, other sustainable C–C and C–heteratom bond-forming concepts will be discussed including fluoroalkylations and isomerizing olefin metatheses. References (a) L. J. Gooßen, G. Deng, L. M. Levy, Science 2006, 313, 662–664. (b) S. Bhadra, W. I. Dzik, L. J. Gooßen, Angew. Chem. Int. Ed. 2013, 52, 2959–2962. (c) B. Bayarmagnai, C. Matheis, K. Jouvin, L. J. Gooßen, Angew. Chem. 2015, 127, 5845-5848. (d) L. Huang, A. Biafora, G. Zhang, V. Bragoni, L. J. Gooßen, Angew. Chem. Int. Ed. 2016, 55, 6933–6937. (e) K. F. Pfister, S. Bader, M. Baader, S. Berndt, L. J. Goossen, Sci. Adv. 2017, 3, e1602624. (f) X.-Q. Hu, Z. Hu, A. S. Trita, G. Zhang, L. J. Gooßen, Chem. Sci. 2018, 9, 5289–5294.