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  • 02월 19일 10시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능
대회명 대한화학회 제121회 학술발표회 및 총회
등록일 2018년 01월 29일 13시 24분 15초
접수번호 3351
발표코드 ORGN.P-326 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간 4월 19일 (목요일) 11:00~12:30
발표형식 포스터
발표분야 Organic Chemistry
저자 및 공동저자 Heejin Kim, Yuya Yonekura, Jun-ichi Yoshida*
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Japan
※ 국외소속으로 등록된 저자의 승인여부는 최소 3일이내 발표자 email로 알려드립니다.
승인 2건
제목 Flow Amination of Organolithiums: Preparation and Synthetic Use of Aminating Reagents Using Flow Microreactors
내용

A synthetic methodology for the formation of C–N bond has become an important subject of considerable attentions in organic synthesis. Various transition-metal-catalyzed coupling reactions have been developed as highly reliable means of carrying out the C–N bond formation as a nucleophilic amination. Electrophilic amination of carbanions (typically, organometallic compounds serves as an alternative tool, which is based on the umpolung strategy. Direct amination of organolithiums has also been studied from the beginning of organolithium chemistry, it still remains an ongoing challenge. The direct amination of organolithiums has suffered from low yields, formations of by-products, and limited scopes, due to an instability and low selectivity of organolithiums. We herein report a design, preparation, and synthetic use of aminating reagents for a rapid amination of functionalized organolithiums in flow microreactors. Various in-situ generated organolithium intermediates could be reacted with optimized aminating reagents in flow for C–N bond formation without using any catalyst under mild conditions in a short time. Based on stopped-flow NMR analysis, the aminating reagent was also prepared by the flow method. The preparation of the aminating reagent was easily optimized without any necessity of work-up. Integrated one-flow synthesis consisting of generation of an aryllithium, the preparation of an aminating reagent, and their reaction was successfully achieved to give desired amine product within 5 min of total reaction time.

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