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제116회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthesis of Fluorenes through Tandem Cu-Catalyzed [3 + 2] Cycloaddition and Rh-Catalyzed Denitrogenative Cyclization in a 5-exo Mode from 2-Ethynylbiaryls and N-Sulfonyl Azides

등록일
2015년 9월 2일 22시 12분 33초
접수번호
1165
발표코드
ORGN.P-402 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 15일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
서보람, 김철의, 이필호*
강원대학교 화학과, Korea
Fluorenes have attracted a great deal of attention due to their optical and electronic properties and their function as π-conjugated materials. They have been widely used as significant privileged structure in a myriad of areas such as optical agents, dyes, organic transistors, and light-emitting devices. Hence, an efficient synthesis of fluorene and its derivatives from easily available compounds has been continuously required. Especially, it is very important to prepare selectively unsymmetrically substituted fluorene derivatives and to introduce substituents at the C-9 methylene bridge of the fluorene moiety without use of base. We report an efficient synthetic method of a wide range of unsymmetric fluorenes having enamine moiety at C-9 methylene bridge from N-sulfonyl-4-biaryl-1,2,3-triazole derivatives via Rh-catalyzed denitrogenative cyclization in a 5-exo mode. Rh-catalyzed denitrogenative cyclization followed by catalytic hydrogenation produces the aminomethyl-substituted fluorenes in a one-pot. Moreover, this protocol can be applied the synthesis of fluorenes via tandem Cu-catalyzed [3 + 2] cycloaddition and Rh-catalyzed denitrogenative cyclization in a 5-exo mode starting from 2-ethynylbiaryls and N-sulfonyl azides in a one-pot.

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