Studies on the formation of C-C and C-N bonds using late transition metal catalysts = 후전이금속 촉매를 이용한 탄소-탄소, 탄소-질소 형성반응에 관한 연구

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Part 1. Copper-Catalyzed Three-Component Reactions 1.Non-Conventional Hydrative Amide Synthesis It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl azides, and water in the presence of copper catalyst and amine base under very mild conditions. The present route is quite general, and a wide range of alkynes and sulfonyl azides are readily coupled catalytically with water to furnish amides in high yields. A variety of labile functional groups are tolerated under the conditions, and the reaction is regioselective in that only terminal alkynes react while double or internal triple bonds are intact. The reaction can be readily scaled up and is also adaptable to a solid-phase procedure with high efficiency. Furthermore, a wide range of propargyl alcohols and sulfonyl azides react to provide β-hydroxy N-sulfonamides in good to excellent yields. Polyhydroxy amides could be synthesized stereoselectively, proving this as a new practical aldol-surrogate strategy. 2.Preparation of 2-Imino Pyrroles A new Cu-catalyzed three-component coupling reaction between 1-alkynes, sulfonyl azides, and pyrrole derivatives has been developed for making 2-functionalized pyrrole rings. This C-C bond formation offers high efficiency and selectivity, mild reaction conditions, and a wide substrate scope. Part 2. Transition-Metal Catalyzed C-H Bond Functionalization: Facile Construction of C-C and C-N Bond 1.Pd-Catalyzed C-H Bond Functionalization of Pyridine N-Oxides Two catalytic protocols of the oxidative C??C bond formation have been developed on the basis of the C-H bond activation of pyridine N-oxides. Pd-catalyzed alkenylation of the N-oxides proceeds with excellent regio-, stereo-, and chemoselectivity, and the corresponding ortho-alkenylated N-oxide derivatives are obtained in good to excellent yields. Direct cross-coupling reaction of pyridine N-oxides w...
Advisors
Chang, Suk-Bokresearcher장석복researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
2011
Identifier
466511/325007  / 020087084
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2011.2, [ iv, 106 p. ]

Keywords

C-H Functionalization; Amide; Copper; Muticomponent Reaction; Carbazole; 카바졸; 탄소-수소 활성화; 아미드; 구리; 다성분짝지움반응

URI
http://hdl.handle.net/10203/31775
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=466511&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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