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제109회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Cyclization of Alkynyl Hydrogen Phosphates Catalyzed by Gold

등록일
2012년 2월 28일 14시 41분 04초
접수번호
1508
발표코드
ORGN.P-959 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
4월 25일 (수요일) 18:00~21:00
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
강동진, 엄다한, 이필호
강원대학교 화학과, Korea
Gold-catalyzed nucleophilic additions to alkynes have attracted a great deal of attention in recent years. These nucleophilic additions include hydroamination, hydration, hydroalkoxylation, hydrocarboxylation as well as the use of other oxygen- or nitrogen- containing nucleophiles such as ketones and imines or even carbon nucleophiles such as C-C double bonds in enols or arenes. Recently, we reported the gold-catalyzed addition of diphenyl phosphate to alkynes to yield vinyl phosphates through the Markovnikov addition. Although the Markovnikov addition is usually observed for termial alkynes, for unsymmetrical alkynes, there is a regioselectivity issue, which is difficult to resolve. In this regard, we have been interested in utilizing alkynyl hydrogen phosphates as temporary phosphate tethers, not only to control the regioseletivity of the cyclization but also to utilize the cyclic phosphate products as coupling partners in transition-metal-catalyzed cross coupling reaction. Herein, we reported an efficient gold-catalyzed cyclization of alkynyl hydrogen phosphates. The cyclization underwent 6-endo-dig, 6-exo-dig, or 7-exo-dig ring closure, depending on the number of carbon atoms present (n=1, 2, 3) between the alkyne and phosphoryl group.

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