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  • 02월 20일 17시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제113회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Metal-Free Protodeboronation of Electron-Rich Arene Boronic Acids and Its Application to ortho-Functionalization of Electron-Rich Arenes Using a Boronic Acids as a Blocking Group

등록일
2014년 2월 13일 16시 45분 30초
접수번호
1153
발표코드
ORGN.O-7 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
금 11시 : 30분
발표형식
구두발표
발표분야
유기화학 - Oral Presentation for Young Organic Chemists
저자 및
공동저자
안수진, 이춘영, 천철홍*
고려대학교 화학과, Korea
Boronic acids are one of the most useful intermediates due to their low toxicity, stability, and ready availability. Although some boronic acids, particularly heteroaromatic boronic acids, are known to unstable, many arene boronic acids are generally believed to be stable and, thus, more than 9000 phenyl boronic acid derivatives are currently commercially available. In contrast to the general belief on the stability of boronic acids, there have been few studies on the actual stability on the boronic acids, and some of the boronic acids, in particular, electron rich arene boronic acids, are not stable even though they are commercially available. For example, we recently found that ortho-and para-phenol boronic acids readily underwent metal-free thermal protodeboronation in wet DMSO, which renders it difficult to store these important boronic acids. With this rather unusual metal-free thermal protodeboronation of phenol boronic acids, we were curious whether this type of metal-free protodeboronation might be the general behaviours of not only phenol boronic acids but also electron-rich boronic acids. Thus, we investigated metal-free thermal protodeboronation of electron-rich arene boronic acids including various reaction parameters to affect the metal-free protodeboronation, such as solvent, electron-density on the arene ring system, acidity of proton source, and Lewis acidity of boron atom in the boronic acid. Based on these results, we established the reaction conditions where the boronic acid functionality could be movable and proposed the reaction mechanism for this protodeboronation. Furthermore, a novel method for the ortho-functionalization of electron-rich arenes has been developed using the boronic acid moiety as a blocking group and subsequent protodeboronation.

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