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제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 An Efficient Synthesis of Quaternary Vinylated Oxindoles by Alkyl to Alkyl Palladium Migration

등록일
2019년 8월 29일 13시 51분 28초
접수번호
1802
발표코드
ORGN.P-435 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 18일 (금요일) 11:00~12:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
Da Sol Chung, Jiwon Hwang, Sang-gi Lee*
Department of Chemistry and Nanoscience (BK 21 PLUS), Ewha Womans University, Korea

Transition metal-catalyzed C-H bond functionalization is widely developed due to its powerful and atom-economic advantage. To enable through-space interaction of a metal center with a neighboring C-H bond, metal migration strategy, including a C-H activation for forming a five membered palladacycle intermediate, has been frequently utilized. However, most reported 1,4-Pd migrations were limited to alkyl C(sp3)-Pd to aryl C(sp2)-Pd or aryl C(sp2)-Pd to aryl C(sp2)-Pd migrations. No research on alkyl C(sp3)-Pd to alkyl C(sp3)-Pd migration was reported. During our recent study on regiodivergent cyclopropanation of σ-alkylPd(II)-intermediate A generated by Heck-type carbopalladation, unprecedented alkyl C(sp3)-Pd to alkyl C(sp3)-Pd migration was observed, from intermediate A to A', and it underwent β-hydride elimination to afford the quaternary vinylated oxindoles 2. To the best of our knowledge, this is the first example of an alkyl to alkyl 1,4-Pd migration.


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