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대한화학회 제112회 학술발표회 및 총회 Ruthenium Catalyzed Redox-Neutral and Single-Step Amide Synthesis from Alcohol and Nitrile with Complete Atom Economy [Reaxys포스터상]

등록일
2013년 8월 28일 22시 38분 04초
접수번호
0692
발표코드
ORGN.P-757 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 16일 (수요일) 16:00~19:00
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
강병준, 홍순혁1,*
서울대학교 화학부, Korea
1서울대학교 화학과, Korea
Atom-economical and environmentally benign amide bond synthesis is one of the top challenges in modern chemistry, especially in pharmaceutical science. To achieve this goal, the avoidance of classical coupling reagents is crucial. Ruthenium catalyzed amide synthesis based on alcohol activation strategy has been under spotlight as a proper alternative of classical method. Here, a completely atom economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrile is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the α-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without any single byproduct. Several mechanistic evidences show that the reaction undergoes with unusual N-unsubstituted imine intermediate followed by hydrogen transfer from alcohol to imine and C-N bond formation. A utility of the reaction was demonstrated by synthesizing 13C or 15N labeled amides, which are important materials in protein structure defining process and metabolism study, without involvement of any separate reduction and oxidation step.

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