Mechanism-driven approaches to site- and enantioselective C−H amidation reactions by developing robust nitrene precursors = 나이트렌 전구체의 개발을 통한 위치 및 거울상 선택적 탄소-수소 아미드화의 반응 메커니즘 기반 연구

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Catalytic functionalization of a carbon-hydrogen to carbon-nitrogen bond is one of the most efficient synthetic transformation to prevalent nitrogen-containing molecules. Although a number of innovative methodologies have been devised for the last decade, fundamental understanding of catalytic mechanism is still infancy and further improvement of the reaction still lie ahead. This dissertation describes the reaction mechanism-guided discovery of novel nitrene precursors and their applications in catalytic C–H amidation protocols, which displayed excellent level of efficiency and selectivity. The important results are (i) development of 1,4,2-dioxazol-5-one compounds as efficient amide agents for (pentamethylcyclopentadienyl)rhodium- and iridium catalysis, (ii) integrated experimental and computational mechanism study for an origin of the reactivity, (iii) leveraging the reactivity of a transient intermediate to envision catalytic C–H insertion reactions and their asymmetric variant, and (iv) applying statistical tools to analyze site- and enantioselectivity of C–H functionalization reactions.
Advisors
Chang, Sukbokresearcher장석복researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2019
Identifier
325007
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2019.2,[vi, 127 p. :]

Keywords

Reaction mechanisms▼aSynthetic methodology▼aTransition metal catalysis▼aAsymmetric catalysis▼aC-H Amidation▼aReaction kinetics▼aDensity functional theory▼aMultivariate analysis; 반응 메커니즘▼a합성적 방법론▼a전이 금속 촉매 작용▼a비대칭성 촉매 작용▼a탄소-수소 아미드화▼a반응 속도론▼a밀도 범함수 이론▼a다변량 분석

URI
http://hdl.handle.net/10203/265500
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=842463&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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