Transition metal-catalyzed C−N bond formation using hydroxamic acid derivatives as the nitrogen source = 하이드로사믹 산 유도체를 질소원으로 사용한 전이금속 촉매 탄소−질소 결합 형성 반응

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For the last decade, C−N bond formation from C−H bonds has been a powerful way of preparing value-added molecules that contain C−N bond. A wide range of nitrogen sources have been utilized in C−N bond formation protocols. Among them, this dissertation describes the applications of N-benzoyloxyamide in catalytic C−H functionalizations. First, an alternative acylnitrenoid precursors for $\gamma$-lactam synthesis was developed. Upon the action of Ir catalysis, N-benzoyloxyamides serve as efficient substrates to afford 5-membered amides via an intramolecular C−H insertion. Mechanistic studies revealed that the generation of a putative Ir-carbonylnitrenoid via N−O bond cleavage is facilitated by the chelation of counter cations. This protocol offers a convenient and step-economic route to $\gamma$-lactams starting from the corresponding carboxylic acids. Second, N-benzoyloxyamide as an amidyl radical source to form oxazoline was investigated. The use of radical species had required energetically demanding condition, making the control of reactions difficult. However, photocatalyst recently showed the possibility to control the radical reaction in benign environment, requiring only visible light as the main energy source. The resulting amidyl radical from N-benzoyloxyamide couples with styrene to form 1,2-aminoalcohol or oxazoline depending on the reaction conditions.
Advisors
Chang, Sukbokresearcher장석복researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2020
Identifier
325007
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 2020.2,[i, 43 p. :]

Keywords

Hydroxylamines▼aC-N bond formation▼aTransition metal catalysis▼aRadical▼aVisible light▼aPhotocatalyst▼aN-benzoyloxyamide▼aAmidyl radical▼aOxazoline▼a1,2-Aminoalcohol; 하이드록실아민▼a탄소-질소 결합 형성▼a전이 금속 촉매 작용▼a라디칼▼a가시광선▼a광촉매▼a엔-벤조일옥시아마이드▼a아미딜 라디칼▼a옥사졸린▼a1,2-아미노알코올

URI
http://hdl.handle.net/10203/283852
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=909933&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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