Development of catalytic 1,2-selective dearomatization of N-heteroarenes = 다양한 촉매 시스템을 이용한 질소 헤테로 방향족의 1,2-선택적 탈방향족화 반응

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Selective dearomatization of N-heteroarenes has recently attracted much interest from researchers because the resulting products are useful building blocks to synthesize valuable pharmaceutical or natural compounds. In this context, the catalyst plays the key role to control the selectivity. In this thesis, we developed 1,2-selective dearomatizations of N-heteroarenes using iridium and N-heterocyclic carbene catalysts. We studied functional group tolerance, mechanism determining the selectivity, and the applicability in our catalytic systems. In the first study, we developed 1,2-hydrosilylation of pyridines and quinolines via transition metal catalyst. While several catalytic systems have been developed for the selective dearomatization of pyridines via 1,4-hydrosilylation, but no catalytic system through 1,2-hydrosilylation has been reported. On the basis of mechanistic assumption, we discovered the first catalytic system for 1,2-hydrosilylation of pyridines and quinolines using commercially available iridium precursor and silane. In the second study, we developed 1,2-hydroboration of quinolines with N-heterocyclic carbene. The previous catalytic systems were problematic in applications toward dearomatization of complex N-heterocycles due to the low regioselectivity and lack of functional group tolerance. To overcome these issues, we developed 1,2-hydroboration of quinolines using neutral Lewis base, N-heterocyclic carbene, displaying the high regioselectivity and good functional group compatibility.
Advisors
Chang, Sukbokresearcher장석복researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2020
Identifier
325007
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2020.8,[iii, 61 p. :]

Keywords

dearomatization of N-heteroarenes▼a1,2-selectivity▼airidium▼aN-heterocyclic carbene▼ahydride insertion; 질소 헤테로 방향족의 탈방향족화▼a1,2-선택성▼a이리듐▼a질소 고리 카빈▼a수소화물 삽입

URI
http://hdl.handle.net/10203/284383
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=924428&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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