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  • 09월 10일 16시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 β-Functionalization of Ketone via Pd-Catalyzed γ-C(sp3) Arylation of Cyclohexylamine with a Transient Directing Group

등록일
2019년 8월 29일 13시 48분 32초
접수번호
1807
발표코드
ORGN.P-437 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 18일 (금요일) 11:00~12:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
Hahyoun Park, Yunyeong Gwon, Byunghyuck Jung1,*
School of Undergraduate Studies, Daegu Gyeongbuk Institute of Science & Technology, Korea
1School of Basic Science, Daegu Gyeongbuk Institute of Science & Technology, Korea

Research of C-H activation has been conducted in worldwide because of its applicability that C-H bond can be exchanged with C-X bond (X= C, O, N, etc.). To activate specific C-H bond, transient directing group is needed for high regioselectivity and efficiency. Therefore, we found the reaction condition and efficient transient directing group to activate γ-C(sp3)-H bond of cyclohexylamine. As a result, 3-bromosalicylaldehyde is the most effective transient directing group in promoting C-H arylation. This reaction progressed with substituted aryl iodides regardless of electronic properties and position of substituent. Both of Electron-rich and electron-deficient aryl iodides afforded the desired products with good yield. In addition, aryl iodides bearing substitutions at the ortho, meta and para position are also well tolerated. Furthermore, C-H arylation proceeded with aliphatic amine, cyclopentyl amine and cycloheptyl amine. To demonstrate the utility of this reaction, further research is being carried out to obtain desired ketone product from substituted amine. Ketone is an important precursor in organic chemistry. Herein we have synthesized β- substituted ketone from γ-substituted amine compound. Substituted amine compound oxidized to imine using TPAP and NMO. Then imine compound converted to ketone after adding hydrochloric acid solution. To synthesize β- substituted ketone, 1,4-addition of enone using Gilman reagents is usually used. However, when Gilman reagents have electrophilic substituent such as carbonyl group, desirable ketone cannot be obtained. Through this reaction, diverse arylated ketone can be synthesized with any substituent regardless of its electronic properties.


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