Mechanism-guided development of nitrenoid transfer catalysts for selective formation of N-heterocycles = 신규한 전이금속 촉매 개발을 통한 나이트렌 이동 반응과 이를 활용한 선택적 헤테로고리 화합물 합성에 관한 연구

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Transition-metal catalyzed nitrene transfer is the most desirable strategies to introduce nitrogen functionality into organic molecules, which allows straightforward and shortcut access to many N-heterocycles. Although tremendous progress has been made in the past decade, the formation of cyclic amides has traditionally been hindered by competing isocyanate formation. This dissertation describes how the reaction mechanism guided to provide an innovative solution to the unmet challenge in contemporary catalysis. Based on the mechanistic understanding derived from a seamless collaboration between theory and experiment, we developed customized transition metal catalysts, which enable to insert metal-nitrenoid into diverse functional groups with the exceptional selectivity. The approach was successfully utilized to develop several synthetic methodologies: (i) selective formation of 5-membered amides via C−H amidation, (ii) stereoselective haloamidation of alkynes by ligand participation, (iii) harnessing Ir-nitrenoid as a motif of 1,3-dipole for stereodefined procedure via olefin difunctionalization, (iv) oxidative cyclization based on the intermediacy of carbocation for allyl amide synthesis and its asymmetric variant, (v) [4+2] and [4+1] annulations.
Advisors
Chang, Sukbokresearcher장석복researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2020
Identifier
325007
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2020.2,[vi, 124 p. :]

Keywords

Transition metal catalysis▼aMetal-nitrenoid transfer▼aCatalyst development▼aC−H Amidation▼aStoichiometric study▼aComputer modeling▼aSynthetic methodology; 메탈-나이트레노이드 전이 반응▼a전이 금속 촉매 작용▼a촉매 개발▼a탄소-수소 아미드화▼a당량 연구▼a컴퓨터 모델링▼a합성적 방법론

URI
http://hdl.handle.net/10203/283466
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=901551&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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