Facile Installation of amino functionality to phosphine oxides and quinoline oxides via direct C-H activation = 탄소-수소 결합 활성화를 통한 포스핀 옥사이드, 퀴놀린 옥사이드의 아미노 작용기 도입 방법 연구

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Organophosphorus containing aniline functionalities and quinolines containing amino functionalities are important structural motif in various area. Nevertheless, organophosphorus and quinoline substrates had no efficient C-N bond introducing method yet. In this paper, we developed direct C-H amidation processes of organophosphorus and quinolines using P or N-oxide as stepping stone. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to P-stereogenic center based on mechanistic consideration. Also, a practical amidating reagents were developed for 8-aminoquinolines. This approach is highly convenient to perform under mild conditions on the gram scale. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.
Advisors
Chang, Sukbokresearcher장석복researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2018
Identifier
325007
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2018.2,[i, 64 p. :]

Keywords

C-N bond formation▼aorganophosphorus▼aasymmetric C-H functionalization▼a8-aminoquinoline; 탄소-질소 결합 형성▼a유기인 화합물▼a비대칭 탄소-수소 작용기화▼a8-아미노퀴놀린

URI
http://hdl.handle.net/10203/265497
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=734455&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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